Diisobutylaluminumhydride → (E,E)-5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadien-1-ol

HRID 1584332Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:23]=[CH:24]/[CH:25]=[CH:26]/[C:27](OC)=[O:28])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].[H-].C([Al+]CC(C)C)C(C)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:23]=[CH:24]/[CH:25]=[CH:26]/[CH2:27][OH:28])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16]

Participants

Reactant 2

HCID 21225700Diisobutylaluminumhydride

HCID 131721330methyl (E,E)-5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadienoate

Product 1

HCID 21224491(E,E)-5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadien-1-ol

Procedure

In substantially the same manner as in Reference Example 24, methyl (E,E)-5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadienoate was subjected to reduction with diisobutylaluminum hydride to yield (E,E)-5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadien-1-ol, which was recrystallized from ethyl acetate to give colorless needles, m.p.149-151° C.

Sources & evidence

ORD record: ord-272b07e0465d4a38994f3c4d69c4453c
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932601

Reaction notes

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