Diisobutylaluminumhydride → (E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol

HRID 233299Notes

Reaction equation

HRID 233299 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH:18]=[CH:19][C:20](OCC)=[O:21].[H-].C([Al+]CC(C)C)C(C)C>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17](/[CH:18]=[CH:19]/[CH2:20][OH:21])[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 53825120Ethyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate

Product 1

HCID 10860209(E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol

Procedure

According to the method described for Reference Example 23, ethyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate was subjected to reduction with diisobutylaluminum hydride to give (E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propen-1-ol. Recrystallization from ethyl acetate gave colorless prisms, m.p.120°-121° C.

Sources & evidence

ORD record
ord-365e897cea584c608ba2cc735885d5e3
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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