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

HRID 1268311Notes

Reaction equation

CC(C[AlH]CC(C)C)C.[F:10][C:11]([F:37])([F:36])[C:12]1[CH:13]=[C:14]([C:22]2[CH:27]=[CH:26][C:25](/[C:28](/[CH3:35])=[CH:29]/[C:30](OCC)=[O:31])=[CH:24][CH:23]=2)[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1>>[F:10][C:11]([F:36])([F:37])[C:12]1[CH:13]=[C:14]([C:22]2[CH:23]=[CH:24][C:25](/[C:28](/[CH3:35])=[CH:29]/[CH2:30][OH:31])=[CH:26][CH:27]=2)[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1

Participants

Reactant 2

HCID 14487Diisobutylaluminum hydride

HCID 22557698(E)-ethyl 3-(3',5'-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enoate

Product 1

HCID 20765801(E)-3-(3',5'-bis-trifluoromethyl-biphenyl-4-yl)-but-2-en-1-ol

Procedure

The colourless solid (E)-3-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-but-2-en-1-ol was prepared by DIBAL-H reduction of (E)-ethyl 3-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enoate by a procedure analogous to that described in example 50b.

Sources & evidence

ORD record: ord-5e7a2fcc38f9447db8a537029de9e999
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555577B1

Reaction notes

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