Sodium bis(2-methoxyethoxy)aluminiumhydride → (E)-1-(3-(Benzyloxy)phenyl)but-2-en-1-ol

温度

0 °C

To a cold solution of sodium bis(2-methoxyethoxy)aluminum hydride (65+ wt. % in toluene) (available from Aldrich) (14.8 mL, 49.1 mmol) in ether (60 mL) was added a solution of 93.A (6.20 g, 24.6 mmol) in ether (30 mL) dropwise under nitrogen at 0° C. The mixture was stirred for 5 minutes at 0° C., the cooling bath was removed, and stirring was continued for 3 hours at room temperature. The reaction was carefully quenched at 0° C. with EtOAc, diluted with saturated aqueous Rochelle salt, and extracted with additional EtOAc. The combined organics were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 93.B (5.37 g, 86% yield) as a colorless oil.

1. customthe cooling bath was removed
2. stirringstirring
3. waitwas continued for 3 hours at room temperature
4. customThe reaction was carefully quenched at 0° C. with EtOAc
5. additiondiluted with saturated aqueous Rochelle salt
6. extractionextracted with additional EtOAc
7. washThe combined organics were washed with water and brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated
10. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

ORDレコード

ord-aa32dbddf9e44890a239782237168f65

出典データセット

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08030354B2