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

HRID 2180503Notes

Reaction equation

HRID 2180503 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH2:16][CH3:17])=[CH:9][C:10]([CH3:15])([CH3:14])[O:11]2)=[CH:6][C:5]=1/[C:18](/[CH3:26])=[C:19](/[F:25])\[C:20](OCC)=[O:21])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH2:16][CH3:17])=[CH:9][C:10]([CH3:14])([CH3:15])[O:11]2)=[CH:6][C:5]=1/[C:18](/[CH3:26])=[C:19](/[F:25])\[CH2:20][OH:21])[CH3:2]

Participants

3

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86597830ethyl (2E)-3-(7-ethoxy-4-ethyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate2×

Product 1

HCID 22491000(2E)-3-(7-Ethoxy-4-ethyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-en-1-ol

Procedure

Following General Procedure L, ethyl (2E)-3-(7-ethoxy-4-ethyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate (Compound 71, 348 mg, 0.96 mmol) and diisobutylaluminum hydride (1 M dichloromethane, 2.9 mL, 2.88 mmol) were reacted to give the title compound as yellow solid after purification by flash chromatography (silica gel, 1:9 to 1:4 ethyl acetate/hexane).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3cd2995d57ae4f5881dad8c5a82ce078
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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