Diisobutylaluminumhydride → (E)-3-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2-propen-1-ol

HRID 233314Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:30]=[CH:29][C:22]([CH:23]=[CH:24][C:25](OC)=[O:26])=[CH:21][CH:20]=1.[H-].C([Al+]CC(C)C)C(C)C>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22](/[CH:23]=[CH:24]/[CH2:25][OH:26])=[CH:29][CH:30]=1

Participants

Reactant 2

HCID 21225700Diisobutylaluminumhydride

HCID 54323026Methyl 4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]cinnamate

Product 1

HCID 23361385(E)-3-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2-propen-1-ol

Procedure

According to the method described for Reference Example 23, methyl 4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]cinnamate was subjected to reduction with diisobutylaluminum hydride to give (E)-3-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2-propen-1-ol. Recrystallization from chloroform-ether gave colorless prisms, m.p.159°-160° C.

Sources & evidence

ORD record: ord-0de606c67d2a4d1cb8e810b1f0acfd0c
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05591862

Reaction notes

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