Diethyl Ether → Ethyl 4-(2-carboxycyclopropyl)-2,3,5-trifluorobenzoate

HRID 981269ノート

反応式

HRID 981269 の反応式
FC(F)(F)C(O)=O.C([O:12][C:13]([C:15]1(C(OC(C)(C)C)=O)[CH2:17][CH:16]1[C:18]1[C:28]([F:29])=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([F:30])[C:19]=1[F:31])=[O:14])(C)(C)C.C(OCC)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:13]([CH:15]1[CH2:17][CH:16]1[C:18]1[C:28]([F:29])=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([F:30])[C:19]=1[F:31])([OH:14])=[O:12]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 15136261HCID 15136261、化合物

生成物 1

HCID 15136262Ethyl 4-(2-carboxycyclopropyl)-2,3,5-trifluorobenzoate収率 54.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

18 ml of trifluoroacetic acid was added to 9.3 g of ethyl 4-(2,2-di-tert-butoxycarbonylcyclopropyl)- 2,3,5-trifluorobenzoate. The resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure. The residue obtained was directly heated with a burner for about 20 seconds to complete decarboxylation. To the reaction mixture were added 100 ml of diethyl ether and 200 ml of water in this order. The resulting mixture was adjusted to pH 9.5 with a 10% aqueous sodium carbonate solution. The aqueous layer was separated and 100 ml of diethyl ether was added thereto. The resulting mixture was adjusted to pH 1.5 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 3.30 g (yield: 54.7%) of ethyl 4-(2-carboxycyclopropyl)-2,3,5-trifluorobenzoate.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue obtained
  3. temperaturewas directly heated with a burner for about 20 seconds
  4. customThe aqueous layer was separated
  5. addition100 ml of diethyl ether was added
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-8c348250841941a0a07efd7478c23b65
出典データセット
uspto-grants-1991_02
特許番号
US04990508

反応ノート

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