Triethyl phosphonoacetate → HCID 54531526, compound

HRID 648651Notes

Reaction equation

HRID 648651 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][C:22]([CH2:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)=[O:23])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:4][CH:3]=1.C(OP([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])(OCC)=O)C.[H-].[Na+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][C:22]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([CH:29]=[CH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:31][CH:32]=2)=[O:23])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 201452794-{N-[alpha-(4-Methyl-phenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzaldehyde

Product 1

HCID 54531526HCID 54531526, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Four hundred twenty-seven milligrams (1 m mol) of 4-{N-[α-(4-methyl-phenyl)-2-piperidino-benzyl]-aminocarbonylmethyl}-benzaldehyde were added to an ethereal solution of 450 mg (2 m mol) of ethyl diethylphosphonoacetate and 100 mg (2 m mol) of 50% sodium hydride. After the mixture had been stirred overnight, water was added, and the resulting mixture was extracted with chloroform and purified by column chromatography on silica gel by use of toluene/ethyl acetate (5:1) as eluant.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. custompurified by column chromatography on silica gel by use of toluene/ethyl acetate (5:1) as eluant

Sources & evidence

ORD record
ord-828fc497bf7f4aa4b10334a63f3ec46d
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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