Triethylamine → Triphenylsulfonium 2-(2,2-dimethylpropionyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate

HRID 2061313노트

반응식

HRID 2061313 반응식
[F:1][C:2]([F:15])([F:14])[C:3]([OH:13])([C:9]([F:12])([F:11])[F:10])[CH2:4][S:5]([O-:8])(=[O:7])=[O:6].[C:16]1([S+:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.[C:42](Cl)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:44][C:43]([CH3:46])([CH3:45])[C:42]([O:13][C:3]([C:2]([F:1])([F:14])[F:15])([C:9]([F:12])([F:10])[F:11])[CH2:4][S:5]([O-:8])(=[O:7])=[O:6])=[O:47].[C:29]1([S+:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86644254Triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

생성물 1

HCID 86644256Triphenylsulfonium 2-(2,2-dimethylpropionyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate수율 59.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Into a mixture solution of 2.6 g (5 mmoles) of triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate prepared in Synthesis Example 1-9, 0.63 g (6 mmoles) of triethylamine, 0.12 g (1 mmole) of 4-dimethylaminopyridine, and 15 g of methylene chloride was added 0.72 g (6 mmoles) of pivaloyl chloride, and they were stirred at room temperature for 8 hours. Thereafter, the reaction was terminated by adding 11 g of 5% hydrochloric acid, and then the organic layer was separated, washed by water, and concentrated under reduced pressure. Into the concentrated solution was added a mixture solution of methyl isobutyl ketone and methylene chloride, and the resulted mixture was concentrated again under reduced pressure to distil the remaining water out. The obtained residue was recrystallized by adding diisopropyl ether, and then the crystals were recovered and dried to obtain the intended triphenylsulfonium 2-(2,2-dimethylpropionyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate (1.8 g of white crystals (yield 58%)). The structure of the intended product is shown below.

후처리

  1. customThereafter, the reaction was terminated
  2. additionby adding 11 g of 5% hydrochloric acid
  3. customthe organic layer was separated
  4. washwashed by water
  5. concentrationconcentrated under reduced pressure
  6. additionInto the concentrated solution was added a mixture solution of methyl isobutyl ketone and methylene chloride
  7. concentrationthe resulted mixture was concentrated again under reduced pressure
  8. customto distil the remaining water out
  9. customThe obtained residue was recrystallized
  10. additionby adding diisopropyl ether
  11. customthe crystals were recovered
  12. customdried

출처 및 근거

ORD 기록
ord-3cf865ca389a4db080f397d64af191ba
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283104B2

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