Ammonium Chloride → 4-(4,4,4-Trifluoro-but-1-enyl)-cyclohexanecarboxylic acid methyl ester

HRID 1755026

반응식

HRID 1755026 반응식
C([Li])CCC.[I-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])C=CC=CC=1.[CH3:32][O:33][C:34]([CH:36]1[CH2:41][CH2:40][CH:39]([CH:42]=O)[CH2:38][CH2:37]1)=[O:35].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:32][O:33][C:34]([CH:36]1[CH2:41][CH2:40][CH:39]([CH:42]=[CH:14][CH2:15][C:16]([F:19])([F:18])[F:17])[CH2:38][CH2:37]1)=[O:35]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 11252253Methyl 4-formylcyclohexane-1-carboxylateHCID 19694095Triphenyl(3,3,3-trifluoropropyl)phosphanium iodideHCID 178418339Butyllithium

생성물 1

HCID 668183484-(4,4,4-Trifluoro-but-1-enyl)-cyclohexanecarboxylic acid methyl ester수율 74%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

A 1.6 M solution of n-butyllithium in hexane (2.5 mL) was added dropwise to a suspension of triphenyl-(3,3,3-trifluoro-propyl)-phosphonium iodide (1.90 g, 3.91 mmol) in tetrahydrofuran (14 mL) at 0° C. The mixture was stirred at 0° C. for 35 minutes, and a solution of 4-formyl-cyclohexanecarboxylic acid methyl ester (605 mg, 3.55 mmol) in tetrahydrofuran (8.0 mL) was then added dropwise to the reaction solution at −78° C. The mixture was stirred for 45 minutes, and a saturated aqueous ammonium chloride solution was then added, followed by extraction with tert-butyl methyl ether. The organic layer was washed with water and a saturated aqueous sodium chloride solution and washed with sodium sulfate. After concentration, the residue was purified by silica gel column chromatography to give 4-(4,4,4-trifluoro-but-1-enyl)-cyclohexanecarboxylic acid methyl ester (657 mg, 67%) as a colorless oily substance and geometric isomer mixture.

후처리

  1. stirringThe mixture was stirred for 45 minutes
  2. extractionfollowed by extraction with tert-butyl methyl ether
  3. washThe organic layer was washed with water
  4. washa saturated aqueous sodium chloride solution and washed with sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b6f4bf81b9cc4eb38f2ba52753ea2943
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

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