Water → Triphenylsulfonium ((1-adamantyl)methoxycarbonyl)difluoromethanesulfonate

HRID 84979

反応式

HRID 84979 の反応式
C([NH3+])(C)(C)C.[C:6]12([CH2:16][O:17][C:18]([C:20]([F:26])([F:25])[S:21]([O-:24])(=[O:23])=[O:22])=[O:19])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.O.[Br-].[C:29]1([S+:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[C:6]12([CH2:16][O:17][C:18]([C:20]([F:26])([F:25])[S:21]([O-:24])(=[O:22])=[O:23])=[O:19])[CH2:15][CH:10]3[CH2:9][CH:8]([CH2:14][CH:12]([CH2:11]3)[CH2:13]1)[CH2:7]2.[C:42]1([S+:35]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

参加物

5

反応物 3

HCID 962WaterHCID 11984010Triphenylsulfonium BromideHCID 131731911(Adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid tert-butylammonium salt

生成物 1

HCID 44224732Triphenylsulfonium ((1-adamantyl)methoxycarbonyl)difluoromethanesulfonate収率 92%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Within a 1-L three-neck flask, 122 g (purity: 99%, 307 mmol, 1.0 eq) of the (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid tert-butylammonium salt obtained in Example 5-b was dissolved in 500 g of chloroform. To the resulting solution, 400 g of water and 110.5 g (322 mmol, 1.05 eq) of triphenylsulfonium bromide were added. This reaction solution was stirred for 1 hour. After the reaction, the reaction solution was separated into an organic layer and an aqueous layer. The organic layer was washed with water, followed by distillating chloroform from the washed organic layer. The thus-obtained concentrated solution was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether and then recrystallized. With this, 166 g of target triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate was obtained (yield: 92%, purity: 99%). No fluorine ion (F−) was detected from any liquid waste of this step. Further, 200 ppb of sodium ion (Na+) was detected from the triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate obtained in this step.

後処理

  1. customAfter the reaction
  2. customthe reaction solution was separated into an organic layer
  3. washThe organic layer was washed with water
  4. dissolutionThe thus-obtained concentrated solution was dissolved in a mixed solvent of chloroform, ethyl acetate and diisopropyl ether
  5. customrecrystallized

出典と根拠

ORDレコード
ord-acfa2cd248d44fc8bd2cb4c3be34f306
出典データセット
uspto-grants-2014_09
特許番号
US08846966B2

関連ノート

読み込み中…