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

HRID 2180501Notes

Reaction equation

[F:1]/[C:2](=[C:8](/[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[O:16][C:15]([CH3:23])([CH3:22])[CH:14]=[C:13]2[CH:24]([CH3:26])[CH3:25])\[CH3:9])/[C:3](OCC)=[O:4].[H-].C([Al+]CC(C)C)C(C)C>>[F:1]/[C:2](=[C:8](/[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[O:16][C:15]([CH3:23])([CH3:22])[CH:14]=[C:13]2[CH:24]([CH3:26])[CH3:25])\[CH3:9])/[CH2:3][OH:4]

Participants

Reactant 2

HCID 21225700Diisobutylaluminumhydride

HCID 86759706ethyl (2E)-2-fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-enoate2×

Product 1

HCID 22490960(2E)-2-Fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-en-1-ol

Procedure

Following General Procedure L, ethyl (2E)-2-fluoro-3-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-but-2-enoate (Compound 69, 145 mg, 0.40 mmol) and a diisobutylaluminum hydride (1M in hexanes, 1.60 mL, 1.60 mmol) were reacted to give the title compound as a colorless oil after purification by flash chromatography (silica gel, 1:9 to 1:4 ethyl acetate/hexane).

Sources & evidence

ORD record: ord-65deb514c6014ea490cd22b033619e6c
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887896B1

Reaction notes

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