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

HRID 515802ノート

反応式

HRID 515802 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 220330274,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate収率 91.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45186e51e05b47b7a00aa3bd76654222
出典データセット
uspto-grants-2015_08
特許番号
US09108944B2

反応ノート

読み込み中…