Triethylamine → (R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate

HRID 1195091

反応式

HRID 1195091 の反応式
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[C@H:20]([OH:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(Cl)Cl>[F:18][C:19]([F:28])([F:29])[C@H:20]([O:27][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2779099(R)-(+)-1,1,1-Trifluoro-2-octanolHCID 37664104-Benzyloxybenzoylchloride

生成物 1

HCID 22850730(R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate収率 65.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To 5 ml of a methylene chloride solution containing 0.56 g of 4-benzyloxybenzoic acid chloride was slowly added a solution of 0.38 g of (R)-(+)-1-trifluoromethylheptanol and 0.23 g of triethylamine in 5 ml of methylene chloride under ice-cooling. The mixture was allowed to warm to room temperature and stirred at that temperature for 12 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride phase was washed successively with diluted hydrochloric acid, water, an aqueous 1N sodium carbonate solution, and water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residual crude product was purified by silica gel column chromatography to obtain 0.53 g of (R)-(+)-4-benzyloxybenzoic acid 1-trifluoromethylheptyl ester.

後処理

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride phase was washed successively with diluted hydrochloric acid, water
  4. dry with materialan aqueous 1N sodium carbonate solution, and water and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe residual crude product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-58a09efc368340d4a7a3508279458c22
出典データセット
uspto-grants-1992_05
特許番号
US05110497

関連ノート

読み込み中…