N-Methyl-N-nitrosourea → Ethyl 4-(1-diphenylmethoxycarbonyl-2-methylvinyl)-2,3,5-trifluorobenzoate

HRID 981262

Reaction equation

HRID 981262 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:8][C:9]([C:11]([C:13]2[C:23]([F:24])=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([F:25])[C:14]=2[F:26])=[CH2:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:35])=[N-].C(OCC)C.CN(N=O)C(N)=O>C(OCC)C.C1(C)C=CC=CC=1>[C:27]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][C:9]([C:11]([C:13]2[C:23]([F:24])=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([F:25])[C:14]=2[F:26])=[CH:12][CH3:35])=[O:10])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 12699N-Methyl-N-nitrosoureaHCID 10094769Ethyl 4-(1-diphenylmethoxycarbonylvinyl)-2,3,5-trifluorobenzoateHCID 21186548Diazomethane diethylether

Product 1

HCID 53699771Ethyl 4-(1-diphenylmethoxycarbonyl-2-methylvinyl)-2,3,5-trifluorobenzoateYield 91.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

In 30 ml of diethyl ether was dissolved 3.08 g of ethyl 4-(1-diphenylmethoxycarbonylvinyl)-2,3,5-trifluorobenzoate. To the resulting solution was added, with ice-cooling, a diazomethane-diethyl ether solution prepared from 2.00 g of N-methyl-N-nitrosourea. The resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure. The residue obtained was dissolved in 30 ml of toluene. The resulting solution was stirred at 60° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene) to obtain 2.90 g (yield: 91.2%) of ethyl 4-(1-diphenylmethoxycarbonyl-2-methylvinyl)-2,3,5-trifluorobenzoate.

Workup

  1. additionTo the resulting solution was added, with ice-
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue obtained
  5. stirringThe resulting solution was stirred at 60° C. for 1 hour
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by a column chromatography (eluant: toluene)

Sources & evidence

ORD record
ord-7bcda04aa6404bc5b49aa9278aab87c3
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Linked notes

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