Diethyl Ether → (7-Isopropylidene-2,5-dimethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol

Reaction equation

[C:1](=[C:4]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5]1)([CH3:3])[CH3:2].O=C[C:12](=[CH2:14])[CH3:13].[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:21]([O:23]CC)C>>[C:1](=[C:4]1[CH:5]2[C:12]([CH3:14])=[CH:13][CH:8]1[C:7]([CH2:21][OH:23])([CH3:9])[CH2:6]2)([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 3283Diethyl Ether2×

HCID 6562Methacrolein

HCID 143632822,6,6-Trimethylfulvene

HCID 21226445Aluminium lithium hydride

Product 1

HCID 22057677(7-Isopropylidene-2,5-dimethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol

Procedure

A mixture of 5-isopropylidene-2-methyl-cyclopenta-1,3-diene (26.4 g, 0.22 mol) and methacroleine (29.4 g, 0.42 mol) were stirred for 2 days at room temperature. The mixture was diluted with diethyl ether (50 ml) and added dropwise at 0° C. to a suspension of LiAlH4 (6.25 g, 0.16 mol) in ether (100 ml). After having been stirred for 1 h at room temperature, the mixture was dropwise quenched successively with water (6 ml), NaOH (15%, 6 ml) and water (6 ml). The mixture was filtered, concentrated in vacuo and the residue was purified by chromatography on silica gel (hexane:MTBE=9:1) to yield 21.6 g of a colorless oil.