Trifluoroacetic acid → HCID 56620230, compound

HRID 746010Notes

Reaction equation

HRID 746010 reaction equation
[CH3:1][O:2][C:3]([C:13]#[N:14])=[CH:4][CH:5]1[CH:7]([C:8]([O-:10])=[O:9])[C:6]1([CH3:12])[CH3:11].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:13]#[N:14])=[CH:4][CH:5]1[CH:7]([C:8]([OH:10])=[O:9])[C:6]1([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86740914HCID 86740914, compound

Product 1

HCID 56620230HCID 56620230, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3 g of tert-butyl (1R,trans ΔZ) 3-(2-methoxy-2-cyanoethenyl)-2,2-dimethyl-cyclopropane carboxylate were dissolved in 60 ml of methylene chloride and 14.6 ml of trifluoroacetic acid were introduced slowly at 0° C. with stirring for 3 hours at 0° C. The mixture was evaporated to dryness by distillation under reduced pressure and cyclohexane was added to the residue. The mixture was again evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a mixture of hexane and ethyl acetate (4/6) yielded 2.05 g of (1R,trans,ΔZ) 3-(2-methoxy-2-cyanoethenyl)-2,2-dimethyl-cyclopropane carboxylic acid melting at 110° C.

Workup

  1. customThe mixture was evaporated to dryness by distillation under reduced pressure and cyclohexane
  2. additionwas added to the residue
  3. customThe mixture was again evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution
  6. additionwith a mixture of hexane and ethyl acetate (4/6)

Sources & evidence

ORD record
ord-e0a3284d52b0435a896c4e6f81d68381
Source dataset
uspto-grants-1986_07
Patent number
US04602038

Reaction notes

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