Sodium Iodide → Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(4-methacryloyloxy-butyryloxy)-propane-1-sulfonate

HRID 556246

반응식

HRID 556246 반응식
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]([C:16]([F:19])([F:18])[F:17])[C:9]([F:15])([F:14])[S:10]([O-:13])(=[O:12])=[O:11])=[O:6].[C:20]1([S+:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:39]([O-:44])(=[O:43])[C:40]([CH3:42])=[CH2:41].[Na+].[I-].[Na+].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)C1C(O)=C(C(C)(C)C)C=C(C)C=1>ClCCl.O.CN(C)C=O>[F:14][C:9]([F:15])([S:10]([O-:13])(=[O:12])=[O:11])[CH:8]([O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][O:44][C:39](=[O:43])[C:40]([CH3:42])=[CH2:41])[C:16]([F:19])([F:18])[F:17].[C:33]1([S+:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)HCID 3255932Sodium methacrylateHCID 86639509Triphenylsulfonium 2-(4-chlorobutyryloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

생성물 1

HCID 86639511Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(4-methacryloyloxy-butyryloxy)-propane-1-sulfonate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

To 20 g of dimethylformamide were added 5.4 g (9.0 mmol) of triphenylsulfonium 2-(4-chlorobutyryloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example 1-20, 1.2 g (11 mmol) of sodium methacrylate, 0.20 g (1.4 mmol) of sodium iodide, and 1 mg of 2,2′-methylenebis(6-t-butyl-p-cresol). The mixture was heated and stirred at 90° C. for 12 hours. The reaction solution was allowed to resume room temperature, after which 50 g of water and 80 g of dichloromethane were added. The organic layer was separated and washed with water whereupon dichloromethane was distilled off under vacuum. The residue was combined with 30 g of methyl isobutyl ketone and washed with water whereupon methyl isobutyl ketone was distilled off under vacuum. The residue was purified by silica gel chromatography. The target compound, triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(4-methacryloyloxy-butyryloxy)-propane-1-sulfonate was obtained as brown oil (4.2 g, yield 72%). The compound has the following structure.

후처리

  1. temperatureThe mixture was heated
  2. customto resume room temperature
  3. customThe organic layer was separated
  4. washwashed with water whereupon dichloromethane
  5. distillationwas distilled off under vacuum
  6. washwashed with water whereupon methyl isobutyl ketone
  7. distillationwas distilled off under vacuum
  8. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-7d4dbbd4c503453a849660fd9226dbcb
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08057985B2

연결된 노트

불러오는 중…