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

HRID 84976

반응식

HRID 84976 반응식
C([NH+](CC)CC)C.[C:8]12([CH2:18][O:19][C:20]([C:22]([F:28])([F:27])[S:23]([O-:26])(=[O:25])=[O:24])=[O:21])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.O.[Br-].[C:31]1([S+:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)(Cl)Cl>[C:8]12([CH2:18][O:19][C:20]([C:22]([F:28])([F:27])[S:23]([O-:26])(=[O:24])=[O:25])=[O:21])[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2.[C:44]1([S+:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11984010Triphenylsulfonium BromideHCID 131731910(Adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid triethylammonium salt

생성물 1

HCID 44224732Triphenylsulfonium ((1-adamantyl)methoxycarbonyl)difluoromethanesulfonate수율 92%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Within a 1-L three-neck flask, 100 g (purity: 93%, 219 mmol, 1.0 eq) of the (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonic acid triethylammonium salt obtained in Example 1-c was dissolved in 300 g of chloroform. To the resulting solution, 250 g of water and 78.9 g (223 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, 119 g of target triphenylsulfonium (adamantane-1-ylmethyl)oxycarbonyldifluoromethanesulfonate was obtained (yield: 92%, purity: 99%).

후처리

  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

출처 및 근거

ORD 기록
ord-d6bb2c220ef44b70a03283ff2acd87a6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846966B2

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