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

HRID 569514ノート

反応式

HRID 569514 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a0d1cf4ce9134eb298d8fcc1737a0a56
出典データセット
uspto-grants-1988_03
特許番号
US04732903

反応ノート

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