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

HRID 556246

反応式

HRID 556246 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7d4dbbd4c503453a849660fd9226dbcb
出典データセット
uspto-grants-2011_11
特許番号
US08057985B2

関連ノート

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