Aluminium lithium hydride → 4-(2-Fluorobenzyl)cyclohexylmethanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH2:13][CH2:12]1)=O>O1CCCC1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][CH:14]1[CH2:13][CH2:12][CH:11]([CH2:9][OH:8])[CH2:16][CH2:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a dry 50 mL 1 neck round bottom flask, lithium aluminium hydride (150 mg; 4.0 mmol) was suspended in dry tetrahydrofuran at 0° C. under nitrogen flow. Dissolved 4-(2-fluorobenzyl)cyclohexanecarboxylic acid methyl ester was added over 2 minutes and mixture was allowed to warm to room temperature. After 3 hours at room temperature, Reaction was quenched with at 0° C. with 0.15 mL of water. After 20 minutes, 0.15 mL of 15% NaOH was added. Finally, 0.45 mL of water was added and continued to stir at 0° C. for 20 minutes. White precipitate was filtered off and rinsed twice with 10 mL ethyl acetate each. Filtrate was concentrated to an oil. Oil was purified by flash chromatography (13:1) and eluted with 10-15% ethyl acetate in hexanes to give 161 mg of title compound. (73% yield).