Diisobutylaluminum hydride → (E)-3-(4-iodophenyl)-but-2-en-1-ol

Reaction equation

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

Participants

Reactant 2

HCID 14487Diisobutylaluminum hydride

HCID 11438459(E)-ethyl 3-(4-iodophenyl)-but-2-enoate

Product 1

HCID 11437263(E)-3-(4-iodophenyl)-but-2-en-1-ol

Procedure

(E)-3-(4-Iodophenyl)-but-2-en-1-ol was prepared by DIBAL-H reduction of (E)-ethyl 3-(4-iodophenyl)-but-2-enoate (example 91a) by a procedure analogous to that described in example 50b.

Sources & evidence

ORD record: ord-849e4768ca8f447db4834d91fee6349d
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555577B1

Reaction notes

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