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

HRID 1268298Notes

Reaction equation

CC(C[AlH]CC(C)C)C.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20](/[C:23](/[CH3:30])=[CH:24]/[C:25](OCC)=[O:26])=[CH:19][CH:18]=1>>[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:18]=[CH:19][C:20](/[C:23](/[CH3:30])=[CH:24]/[CH2:25][OH:26])=[CH:21][CH:22]=1

Participants

Reactant 2

HCID 14487Diisobutylaluminum hydride

HCID 22557711(E)-ethyl 3-(2'-methyl-biphenyl-4-yl)-but-2-enoate

Product 1

HCID 22557657(E)-3-(2'-methyl-biphenyl-4-yl)-but-2-en-1-ol

Procedure

The colourless oil (E)-3-(2′-methyl-biphenyl-4-yl)-but-2-en-1-ol was prepared by DIBAL-H reduction of (E)-ethyl 3-(2′-methyl-biphenyl-4-yl)-but-2-enoate by a procedure analogous to that described in example 50b.

Sources & evidence

ORD record: ord-f52beace713749578f91c44ef5cd4f36
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555577B1

Reaction notes

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