Ethyl diazoacetate → HCID 59161500, compound

HRID 1916026Notes

Reaction equation

HRID 1916026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])=[CH2:9])=[CH:4][CH:3]=1.[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>C(O)C(F)(F)F.CC1C(C)=CC2N([C@H]3O[C@H](CO)[C@@H](OP(O[C@@H](CNC(CC[C@]4(C)[C@@H](CC(N)=O)[C@H]5[N-]C4=C(C)C4=NC(C(C)(C)[C@@H]4CCC(N)=O)=CC4=NC([C@](CC(N)=O)(C)[C@@H]4CCC(N)=O)=C(C)C4=N[C@]5(C)[C@](CC(N)=O)(C)[C@@H]4CCC(N)=O)=O)C)([O-])=O)[C@H]3O)C=NC=2C=1.O.[Co+2]>[CH2:17]([O:16][C:14]([CH:13]1[CH2:9][C:8]1([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[F:10])=[O:15])[CH3:18]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 11147850Benzene, 1-chloro-4-(1-fluoroethenyl)-

Product 1

HCID 59161500HCID 59161500, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 5460373HCID 5460373, compoundCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

Vitamin B12a (1.00 g; 0.723 mmol) was dissolved in dry trifluoroethanol (70 ml) and 1-chloro-4-(1-fluoro-vinyl)-benzene (6.50 g; 41.5 mmol) and ethyl diazoacetate (6.30 g; 50 mmol; 90% purity) was added. The solution was stirred, under reflux, under nitrogen atmosphere for 18 h. After cooling the solvent was evaporated and the residue purified by flash chromatography using 9:1 hexane/ethyl acetate. 6.9 g of 2-(4-chlorophenyl)-2-fluoro-cyclopropane carboxylic acid ethyl ester was obtained in the form of an oil (81% of theory) as a 7:3 mixture of cis/trans isomers.

Workup

  1. temperatureunder reflux, under nitrogen atmosphere for 18 h
  2. temperatureAfter cooling the solvent
  3. customwas evaporated
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-1ef303beb713457b91defa35c4d35267
Source dataset
uspto-grants-2013_12
Patent number
US08618023B2

Reaction notes

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