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

HRID 984324Notes

Reaction equation

HRID 984324 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[CH:13]=[CH:12][C:11](/[C:14](/[CH3:21])=[CH:15]/[C:16](OCC)=[O:17])=[CH:10][CH:9]=2)[CH:7]=1.CC(C[AlH]CC(C)C)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[CH:13]=[CH:12][C:11](/[C:14](/[CH3:21])=[CH:15]/[CH2:16][OH:17])=[CH:10][CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22557579(E)-Ethyl 3-(5'-chloro-2'-methoxy-biphenyl-4-yl)-but-2-enoate

Product 1

HCID 69799843(E)-3-(5'-chloro-2'-methoxy-biphenyl-4-yl)-but-2-en-1-ol

Procedure

(E)-Ethyl 3-(5′-chloro-2′-methoxy-biphenyl-4-yl)-but-2-enoate (0.90 g, 2.72 mmol) was reduced with DIBAL-H by a procedure analogous to that described in example 52 b to give (E)-3-(5′-chloro-2′-methoxy-biphenyl-4-yl)-but-2-en-1-ol as a colourless oil; 0.785 g (100%).

Sources & evidence

ORD record
ord-e57100618e3a46d5802f5748bfa634fa
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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