Aluminium lithium hydride → HCID 69907451, compound
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:28])=[CH:22][C:23](OCC)=[O:24])=[CH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[CH:7]1([C:15]2[CH:16]=[CH:17][C:18]([C:21]([CH3:28])=[CH:22][CH2:23][OH:24])=[CH:19][CH:20]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To an ice cooled slurry of LiAlH4 (2.9 g) in dry ether (200 ml) was added a solution of ethyl 3-(4′-cyclooctylphenyl)-but-2-enoate (3d, 10 g) in dry ether (50 ml) dropwise. The reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was quenched with water (11 ml). A solution of 10% NaOH (10 ml) was added and ether layer was decanted. The precipitate was washed with ether and combined extracts were concentrated. The crude product was purified by column chromatography on silica gel to give 6.82 g (79.3% yield) of 3-(4′-cyclooctylphenyl)-2-butenol (4d, formula 4, R=cyclooctyl) m.p. 40-44° C.