Diethyl (cyanomethyl)phosphonate → HCID 23361377, compound

HRID 233311Notes

Reaction equation

HRID 233311 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH:17]=O)=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25]([CH2:27]P(=O)(OCC)OCC)#[N:26]>>[CH3:1][C:2]1[O:6][C:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH:17]=[CH:27]/[C:25]#[N:26])=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 11120755HCID 11120755, compound

Product 1

HCID 23361377HCID 23361377, compound

Procedure

According to the method described for Reference Example 35, (E)-3-[4-(5-methyl-4-phenyl-2-oxazolylmethoxy)phenyl]-2-propen-1-al was allowed to react with diethyl cyanomethylphosphonate to give (E,E)-5-[4-(5-methyl-4-phenyl-2-oxazolylmethoxy)phenyl]-2,4-pentadienenitrile. Then, according to the method described for Reference Example 16, (E,E)-5-[4-(5-methyl-4-phenyl-2-oxazolylmethoxy)phenyl]-2,4-pentadienenitrile was subjected to catalytic reduction to give 5-[4-(5-methyl-4-phenyl-2-oxazolylmethoxy)phenyl]valeronitrile. Recrystallization from ethyl acetate--ether--hexane gave colorless prisms, m.p.65°-66° C.

Sources & evidence

ORD record
ord-dc2e00e60de94267907c19a5e7bbdf72
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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