Aluminum isopropoxide → 2-Ethyl-4-(2',2',3-trimethylcyclopent-3'-enyl)but-2-enol

HRID 363826Notes

Reaction equation

HRID 363826 reaction equation
C(O[Al])(CC)C.CC([O-])C.CC([O-])C.CC([O-])C.[Al+3].[CH2:20]([C:22](=[CH:25][CH2:26][CH:27]1[CH2:31][CH:30]=[C:29]([CH3:32])[C:28]1([CH3:34])[CH3:33])[CH:23]=[O:24])[CH3:21]>>[CH2:20]([C:22](=[CH:25][CH2:26][CH:27]1[CH2:31][CH:30]=[C:29]([CH3:32])[C:28]1([CH3:33])[CH3:34])[CH2:23][OH:24])[CH3:21]

Participants

4

Reactant 3

HCID 11143Aluminum isopropoxideHCID 1032132-Butenal, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-HCID 86753749HCID 86753749, compound

Product 1

HCID 1198982-Ethyl-4-(2',2',3-trimethylcyclopent-3'-enyl)but-2-enolYield 60%

Procedure

The reaction was carried out in the same manner as in Example 1, except that 2.18 g (10 mmol) of sec-butoxyaluminum diisopropylate was used instead of aluminum isopropylate, and 10.3 g (50 mmol) of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-al was used instead of 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-al. After 5 hours, according to GLC analysis, 60% of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol was obtained (corresponding to 87% selectivity for conversion of the aldehyde as the starting material).

Sources & evidence

ORD record
ord-0bb6e1ebfcc548f18d9267580beca1d0
Source dataset
uspto-grants-1999_02
Patent number
US05874649

Reaction notes

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