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. Author manuscript; available in PMC: 2012 Nov 11.
Published in final edited form as: Tetrahedron. 2011 Nov 11;67(45):8607–8614. doi: 10.1016/j.tet.2011.09.036

Table 5.

Effect of molecular sieves amount and the pyrrolidine concentration on the reaction rate

Entrya MS
(g/mm
ol)
Cat.
(mol%)
Solvent %Conversioni
1 0 10 catb MeOH 80 100
2 0.1 10 catb MeOH 74 100
3 0.2 10 catb MeOH 78 100
4 0.3 10 catb MeOH 85 100
5 0.4 10 catb MeOH 84 100
6 0.5 10 catb MeOH 84 100
7 0.7 10 catb MeOH 84 100
8 0 5 catb MeOH 54 84 100
9 0 1 catb MeOH 11 28 58
10 0 0.1 catb MeOH 0 0 0
11 0 0.01 catb MeOH 0 0 0
12 0 40 catc MeOH 0.5e
13 0 80 catc MeOH 5f
14 0 10 catb CH3CN 23 55 89g
15 0 10 catb DMSO 19 48 88g
16 0 10 catb Ether 0 0 0
17 0 10 catb THF 0 0 0
18 0 10 catb,d Ether 0 1 4h
19 0 10 catb,d THF 0 1 4h
a

All entries are for the reactions of 2b with cyclopentadiene in 1:1.2 ratios at room temperature.

b

Catalyst pyrrolidine.

c

Catalyst DEA.

d

200mol% MeOH.

e

The yield after 24 h is 39.

f

66% after 24 h.

g

100% after 24 h.

h

20% after 24 h.

i

Conversion at 0.5h, 1.7h and 5h, respectively.