Aluminium lithium hydride → [3-(3-Methoxypropyl)phenyl]methanol
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9](OCC)=[O:10].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:14]=[CH:15][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a THF solution (0.2 M) of ethyl 3-(3-methoxypropyl)benzoate from the previous step (1 eq.) was added lithium aluminum hydride (1.0 M THF solution, 5 eq.) at 0° C. over a period of 20 min. The resulting suspension was stirred at 0° C. for 1 h and then at RT for 1 h. The reaction was quenched, at 0° C., with the dropwise addition of H2O and then 1 N aq. NaOH. The biphasic mixture was allowed to stir at RT for 10 min, poured into H2O and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a cloudy oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.