Water → 4,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate

HRID 515802노트

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HRID 515802 반응식
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:4][CH2:5][OH:6].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:11])([F:1])[C:7]([F:8])([F:9])[F:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

생성물 1

HCID 220330274,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate수율 91.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 4,4,5,5,5-pentafluoropentan-1-ol (1 g, 5.6 mmol), p-toluenesulfonylchloride (1.3 g, 6.8 mmol), and triethylamine (1.2 mL, 8.4 mmol) in DCM (20 mL) was stirred at room temperature for 18 h. Water was added to the reaction mixture, the two layers were separated, and the aqueous layer was extracted with DCM (2×). The organics were combined, dried over sodium sulfate, and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes to afford 1.7 g of 4,4,5,5,5-pentafluoropentyl 4-methylbenzenesulfonate as a colorless oil.

후처리

  1. customthe two layers were separated
  2. extractionthe aqueous layer was extracted with DCM (2×)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-45186e51e05b47b7a00aa3bd76654222
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108944B2

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