2-(2-Hy­droxy­propan-2-yl)-6-(prop-2-yn­yloxy)-1-benzofuran-3(2H)-one

Henok H Kinfe; Yonas H Belay; Zanele H Phasha

doi:10.1107/S1600536812045606

. 2012 Nov 17;68(Pt 12):o3379. doi: 10.1107/S1600536812045606

2-(2-Hydroxypropan-2-yl)-6-(prop-2-ynyloxy)-1-benzofuran-3(2H)-one

Henok H Kinfe ^a, Yonas H Belay ^a, Zanele H Phasha ^a,^*

PMCID: PMC3588975 PMID: 23476211

Abstract

In the title compound, C₁₄H₁₄O₄, the prop-2-ynyloxy O—C—C C plane [maximum deviation = 0.0116 (12) Å] forms a dihedral angle of 78.44 (9)° with the benzofuran-3(2H)-one ring system. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming a tape along the a-axis direction. C—H⋯O interactions are observed between the tapes.

Related literature

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004 ▶). For details of the synthesis of the title compound, see: Hoogendoorn et al. (2011 ▶). graphic file with name e-68-o3379-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₄O₄
M _r = 246.25
Triclinic,
a = 5.4199 (2) Å
b = 9.0785 (3) Å
c = 12.3555 (4) Å
α = 85.758 (2)°
β = 80.455 (2)°
γ = 81.829 (2)°
V = 592.65 (4) Å³
Z = 2
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 100 K
0.39 × 0.11 × 0.11 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.736, T _max = 0.913
10266 measured reflections
1983 independent reflections
1888 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.082
S = 1.03
1983 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Click here for additional data file.^{(22.9KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045606/is5212sup1.cif

e-68-o3379-sup1.cif^{(22.9KB, cif)}

Click here for additional data file.^{(95.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045606/is5212Isup2.hkl

e-68-o3379-Isup2.hkl^{(95.5KB, hkl)}

Click here for additional data file.^{(4.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812045606/is5212Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H⋯O4ⁱ	0.84	2.01	2.8328 (12)	167
C1—H1⋯O1ⁱⁱ	0.95	2.45	3.3283 (16)	154
C5—H5⋯O1ⁱⁱⁱ	0.95	2.52	3.3809 (15)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

Research funds of the University of Johannesburg is gratefully acknowledged.

supplementary crystallographic information

Comment

In our research in the development of hybrid drug candidates against tuberculosis, malaria and cancer (Morphy et al., 2004), the title compound was synthesized as a building starting material. The title compound was synthesized by the reaction of 6-hydroxy-benzofuran-3-one with propargyl bromide in the presence of potassium carbonate at relatively high temperature (Hoogendoorn et al., 2011). Herein we report the crystal structure of the title compound.

In the crystal structure of the title compound, the propyn-1-yloxy group (C1–C3/O3) forms a dihedral angle of 78.44 (9)° with the fused benzofuran-3-one ring system (Fig. 1). The crystal packing is stabilized by O—H···O interactions (Table 1 and Fig. 2). The C—H···O interactions are also observed (Table 1).

Experimental

A solution of 6-hydroxy-benzofuran-3-one (1 g, 6.66 mmol) in dry acetone was treated with potassium carbonate (1.3 g, 9.32 mmol). The reaction mixture was heated at a temperature of 70–80 °C for about 30 minutes and then propargyl bromide (1.6 ml, 14.65 mmol) was added to it. The combined solution was stirred for about 2.5 h and concentrated under vacuum. The residue was diluted with water and extracted three times with ethyl acetate. The combined organic layer was washed with brine and water and dried over anhydrous magnesium sulfate. After that filtered and the filtrate solid product was recrystalized from ethyl acetate and hexane to afford 70% of the target compound as yellow crystal (m.p. 118–120 °C).