Sodium Hydroxide → Triphenylsulfonium 2,2-difluoro-3-methacryloyloxypentanoate

HRID 471335

反応式

HRID 471335 の反応式
[C:1]([O:6][CH:7]([CH2:14][CH3:15])[C:8]([C:11]([OH:13])=[O:12])([F:10])[F:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH-].[Na+].[Br-].[C:19]1([S+:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[F:9][C:8]([F:10])([CH:7]([O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH2:14][CH3:15])[C:11]([O-:13])=[O:12].[C:32]1([S+:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 11984010Triphenylsulfonium BromideHCID 584134402,2-Difluoro-3-(methacryloyloxy)pentanoic acid

生成物 1

HCID 86657208Triphenylsulfonium 2,2-difluoro-3-methacryloyloxypentanoate収率 101.1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

反応条件

温度
0 °C

実験手順

A 1-L glass flask equipped with a dropping funnel was charged with 108 g (0.486 mol) of 1-hydroxycarbonyl-1,1-difluoro-2-butyl methacrylate and 108 g of chloroform, which were stirred and cooled at 0° C. Then 224 g (0.560 mol/1.15 equivalent) of a 10 wt % sodium hydroxide aqueous solution was added dropwise to the solution, which was stirred at room temperature for 1 hour. Then 169 g (0.492 mol/1.01 equivalent) of triphenylsulfonium bromide in 432 g of chloroform was added to the solution, which was stirred at room temperature for 1 hour. After the completion of reaction was confirmed by 1H-NMR spectroscopy, an organic layer was separated from the reaction liquid and washed 3 times with 300 g of water. The organic layer was concentrated in vacuum, obtaining 238 g (yield 81%, purity 80%) of triphenylsulfonium 2,2-difluoro-3-methacryloyloxypentanoate, designated Monomer Z-1, having the following structure.

後処理

  1. stirringwas stirred at room temperature for 1 hour
  2. stirringwas stirred at room temperature for 1 hour
  3. customAfter the completion of reaction
  4. customan organic layer was separated from the reaction liquid
  5. washwashed 3 times with 300 g of water
  6. concentrationThe organic layer was concentrated in vacuum

出典と根拠

ORDレコード
ord-3df02a539c1841cd823538d1d63b62a2
出典データセット
uspto-grants-2014_01
特許番号
US08632939B2

関連ノート

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