Trimethyl phosphonoacetate → methyl (E,E)-5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadienoate

HRID 1584330Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20])[CH:6]=[CH:7][CH:8]=O.[CH3:27][O:28][C:29]([CH2:31]P(OC)(OC)=O)=[O:30]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:7]/[CH:8]=[CH:31]/[C:29]([O:28][CH3:27])=[O:30])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20]

Participants

Reactant 2

HCID 80029Trimethyl phosphonoacetate

HCID 538228793-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde

Product 1

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

Procedure

In substantially the same manner as in Reference Example 16, 3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde was allowed to react with trimethyl phosphonoacetate to produce methyl (E,E)-5-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadienoate, which was recrystallized from ethyl acetate to give colorless prisms, m.p.166-167° C.

Sources & evidence

ORD record: ord-22d1e603b3ed4ca5a3e826f86c7c89e4
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932601

Reaction notes

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