Aluminium lithium hydride → 3-[3-(3-Hydroxypropyl)phenyl]propan-1-ol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][C:21](OCC)=[O:22])[CH:14]=1)C>C1COCC1>[OH:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of lithium aluminum hydride (1.63 g, 42 mmol) in THF (50 mL) was cooled to 0° C. and the intermediate from Step B (6.0 g, 21 mmol) in THF (50 mL) was added dropwise. After the addition was complete, the reaction mixture was warmed to ambient temperature over 30 minutes. The reaction was quenched by slowly adding 1N HCl (200 mL) and then DCM (400 mL) was added. The organic layer was removed and the aqueous layer was washed with DCM (4×100 mL). The combined organic layers were washed with saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to provide 3.3 g of the title intermediate (81% yield), which was used without further purification.