4-Toluenesulfonyl chloride → 4,4-Dimethyl-2-(4'-p-toluenesulfonyloxymethylbiphenyl-2-yl)oxazoline

HRID 742794

반응식

HRID 742794 반응식
[H-].[Na+].[CH3:3][C:4]1([CH3:23])[CH2:8][O:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=2)=[N:5]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:3][C:4]1([CH3:23])[CH2:8][O:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:16]=[CH:17][C:18]([CH2:21][O:22][S:30]([C:27]3[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=3)(=[O:32])=[O:31])=[CH:19][CH:20]=2)=[N:5]1

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

생성물 1

HCID 153808794,4-Dimethyl-2-(4'-p-toluenesulfonyloxymethylbiphenyl-2-yl)oxazoline수율 55%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

0.34 g (8.5 mmol) of a 60% oily sodium hydride was suspended in tetrahydrofuran (20 ml). A solution of 2.0 g (7.1 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline in tetrahydrofuran (30 ml) was dropwise added thereto at room temperature, followed by further stirring at room temperature for one hour. After the reaction liquid was cooled with ice, a solution of 1.6 g (8.4 mmol) of p-toluene-sulfonyl chloride in tetrahydrofuran (20 ml) was dropwise added thereto. After stirring for 3 hours as such, the reaction liquid was poured into a saturated aqueous solution of ammonium chloride, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 1.7 g of the title compound as an oil (yield 55%).

후처리

  1. customat room temperature
  2. customAfter the reaction liquid
  3. temperaturewas cooled with ice
  4. stirringAfter stirring for 3 hours as such,
  5. customthe reaction liquid
  6. extractionfollowed by the extraction with chloroform
  7. washAfter washing with water
  8. customdrying
  9. concentrationvacuum concentration
  10. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

출처 및 근거

ORD 기록
ord-96efc7470c5c4d81a071bec55ceff6f7
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554757

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