Aluminium lithium hydride → [3-(3-Methoxypropyl)phenyl]methanol

Temperature

0 °C

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.

1. waitat RT for 1 h
2. customThe reaction was quenched, at 0° C., with the dropwise addition of H2O
3. stirringto stir at RT for 10 min
4. additionpoured into H2O
5. extractionextracted with ether
6. washThe combined organic extracts were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customConcentration of the filtrate in vacuo afforded a cloudy oil
10. customPurification of the crude product
11. customthus obtained by way of flash chromatography (SiO2, 7:3 (v/v) Hex:EtOAc)

ORD record

ord-aba70d0ac77f417e8fd19251259f5474

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2