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

HRID 1662568

Reaction equation

[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:29]([OH:33])[C:30]#[C:31][CH3:32])[CH:26]=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOCC>[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:29]([OH:33])/[CH:30]=[CH:31]/[CH3:32])[CH:26]=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-aa32dbddf9e44890a239782237168f65
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Linked notes

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