Quinoline → (1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid

HRID 569514Notes

Reaction equation

HRID 569514 reaction equation
[H][H].[CH3:3][C:4]1([CH3:20])[C@@H:6]([C:7]#[C:8][C:9](=[O:16])[O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[C@H:5]1[C:17]([OH:19])=[O:18].N1C2C(=CC=CC=2)C=CC=1>[OH-].[Pd+2].[OH-].C(OCC)(=O)C>[CH3:3][C:4]1([CH3:20])[C@@H:6](/[CH:7]=[CH:8]\[C:9](=[O:16])[O:10][CH2:11][C:12]([F:15])([F:13])[F:14])[C@H:5]1[C:17]([OH:19])=[O:18]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 13390083(1R,cis) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoroethoxy)-1-propynyl]-cyclopropane-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 13390085(1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acidYield 64.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

500 mg of 10% palladium hydroxide on barium sulfate and 5 ml of ethyl acetate were placed in a round flask connected to a hydrogen apparatus and 2 g of the product of Step C, 45 ml of ethyl acetate and 0.5 ml of quinoline were added thereto. Hydrogenation was carried out until hydrogen absorption ceased and the mixture was filtered. The filtrate was washed with N hydrochloric acid, then with water and evaporated to dryness. The 2 g of residue were chromatographed over silica gel and eluted with a 70-30-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 1.3 g of (1R,cis)2,2-dimethyl-3-[(Z)-3-oxo-3-(2,2,2-trifluoro-ethoxy)-1-propenyl]-cyclopropane-carboxylic acid.

Workup

  1. additionwere added
  2. customHydrogenation was carried out until hydrogen absorption
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with N hydrochloric acid
  5. customwith water and evaporated to dryness
  6. customThe 2 g of residue were chromatographed over silica gel
  7. washeluted with a 70-30-1 cyclohexane-ethyl acetate-acetic acid mixture

Sources & evidence

ORD record
ord-a0d1cf4ce9134eb298d8fcc1737a0a56
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

Loading…