Diisobutylaluminum hydride → (E)-3-(3',5'-dichloro-biphenyl-4-yl)-but-2-en-1-ol

Reaction equation

CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:23]=[CH:22][C:21](/[C:24](/[CH3:31])=[CH:25]/[C:26](OCC)=[O:27])=[CH:20][CH:19]=2)[CH:14]=[C:15]([Cl:17])[CH:16]=1>>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:19]=[CH:20][C:21](/[C:24](/[CH3:31])=[CH:25]/[CH2:26][OH:27])=[CH:22][CH:23]=2)[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

Reactant 2

HCID 14487Diisobutylaluminum hydride

HCID 22557629(E)-ethyl 3-(3',5'-dichloro-biphenyl-4-yl)-but-2-enoate

Product 1

HCID 69795925(E)-3-(3',5'-dichloro-biphenyl-4-yl)-but-2-en-1-ol

Procedure

The colourless oil (E)-3-(3′,5′-dichloro-biphenyl-4-yl)-but-2-en-1-ol was prepared by DIBAL-H reduction of (E)-ethyl 3-(3′,5′-dichloro-biphenyl-4-yl)-but-2-enoate as described for example 52b.

Sources & evidence

ORD record: ord-cb22c7bf59924c1386bd0417c3b355ec
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555577B1

Reaction notes

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