Diisobutylaluminumhydride → (2E)-3-(7-Butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-en-1-ol

HRID 2180506Notes

Reaction equation

HRID 2180506 reaction equation
[CH2:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH:18]([CH3:20])[CH3:19])=[CH:11][C:12]([CH3:17])([CH3:16])[O:13]2)=[CH:8][C:7]=1/[C:21](/[CH3:29])=[C:22](/[F:28])\[C:23](OCC)=[O:24])[CH2:2][CH2:3][CH3:4].[H-].C([Al+]CC(C)C)C(C)C>>[CH2:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH:18]([CH3:19])[CH3:20])=[CH:11][C:12]([CH3:17])([CH3:16])[O:13]2)=[CH:8][C:7]=1/[C:21](/[CH3:29])=[C:22](/[F:28])\[CH2:23][OH:24])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86597833ethyl (2E)-3-(7-butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate2×

Product 1

HCID 22490857(2E)-3-(7-Butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-en-1-ol

Procedure

Following General Procedure L, ethyl (2E)-3-(7-butoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate (Compound 74, 133 mg, 0.34 mmol) and diisobutylaluminum hydride (1 M in hexanes, 1.37 mL, 1.37 mmol) were reacted to give the title compound as a colorless oil after purification by flash chromatography (silica gel, 1:9 ethyl acetate/hexane).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9f113310c7d943e0a768567f17e76a59
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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