Diethyl (cyanomethyl)phosphonate → (E,E)-5-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2,4-pentadienenitrile

HRID 233316Notes

Reaction equation

HRID 233316 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:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH:27]=O)=[CH:21][CH:20]=1.[C:29]([CH2:31]P(=O)(OCC)OCC)#[N:30]>>[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:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH:27]=[CH:31]/[C:29]#[N:30])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23361378(E)-3-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2-propen-1-al

Product 1

HCID 23361381(E,E)-5-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2,4-pentadienenitrile

Procedure

According to the method described for Reference Example 35, (E)-3-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2-propen-1-al was allowed to react with diethyl cyanomethylphosphonate to give (E,E)-5-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]phenyl]-2,4-pentadienenitrile. Recrystallization from ethyl acetate--ether gave colorless prisms, m.p.159°-160° C.

Sources & evidence

ORD record
ord-ba30468fd825454f83f414ac771844e2
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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