Triethylamine → Triphenylsulfonium 2-(2-adamantane-1-yl-acetoxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate

HRID 2061314노트

반응식

HRID 2061314 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:35]12([CH2:45][C:46](Cl)=[O:47])[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:43][CH:37]([CH2:38]3)[CH2:36]1)[CH2:42]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:35]12([CH2:45][C:46]([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])[CH2:42][CH:41]3[CH2:40][CH:39]([CH2:38][CH:37]([CH2:43]3)[CH2:36]1)[CH2:44]2.[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 27718821-Adamantaneacetyl chlorideHCID 86644254Triphenylsulfonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

생성물 1

HCID 86644257Triphenylsulfonium 2-(2-adamantane-1-yl-acetoxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate수율 48.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

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, 1.3 g (6 mmoles) of 1-adamantaneacetyl chloride, and 15 g of methylene chloride was added a mixture solution of 0.63 g (6 mmoles) of triethylamine, 0.12 g (1 mmole) of 4-dimethylaminopyridine, and 5 g of methylene chloride, and they were stirred at room temperature for 5 days. Thereafter, the reaction was terminated by adding 7 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 methyl isobutyl ketone, 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-adamantane-1-yl-acetoxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate (1.7 g of white crystals (yield 48%)). The structure of the intended product is shown below.

후처리

  1. customThereafter, the reaction was terminated
  2. additionby adding 7 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 methyl isobutyl ketone
  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-bdade75d2f0e4798a00dfbf7872660a0
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283104B2

반응 노트

불러오는 중…