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. 2019 Dec 10;15:2948–2957. doi: 10.3762/bjoc.15.290

Table 5.

Green solvents screening for the Ireland–Claisen rearrangement of 1c.

graphic file with name Beilstein_J_Org_Chem-15-2948-i004.jpg
Entry Solvent T (°C) Yield of 3c (%) syn/antia
1 DCM −60 74 69:31
2 2-Me-THF −60 63 71:29
3 CpOMe −60 84 68:32
4 CpOMeb −60 73 70:30
5 PhCF3 −20 76 69:31
6 CH3OCH2CH2OCH3 −50 58 70:30
7 CH3CN −60 11 n.d.
8 – −60 95 69:31
9 –b −60 73 70:30

aBoth diastereomers were obtained as a racemic mixture. bReaction carried out in the presence of C6 (10 mol %).