p-Toluenesulfonic acid → HCID 54008977, 화합물

HRID 464641노트

반응식

HRID 464641 반응식
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[N:9][OH:10])[S:2]2.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:10][N:9]=[C:3]1[CH:4]2[CH2:7][CH2:8][CH:1]([CH:6]=[CH:5]2)[S:2]1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 71415470N-2-Thiabicyclo[2.2.2]oct-5-en-3-ylidenehydroxylamine

생성물 1

HCID 54008977HCID 54008977, 화합물수율 93.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 10 g (0.06 m) of 2-thiabicyclo[2.2.2]oct-5-en-3-one oxime, 9 g (0.1 m) of 98% dihydropyran, and a catalytic amount of p-toluenesulfonic acid in 30 ml of methylene chloride was heated under reflux overnight. Sodium bicarbonate was added to neutrality. The residue after removal of solvent was purified by dry column chromatography (silica gel-ethyl acetate:hexane::1:1) to give 14.4 g of yellow solid. Recrystallization from ether-hexane yielded 10.1 g of the title compound as a white solid, m. 84°-5° C.

후처리

  1. temperatureunder reflux overnight
  2. customThe residue after removal of solvent
  3. customwas purified
  4. dry with materialby dry column chromatography (silica gel-ethyl acetate:hexane::1:1)

출처 및 근거

ORD 기록
ord-6fd33b4799be44808983ea32d19c9adb
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548929

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