p-Toluenesulfonic acid → HCID 54008977、化合物

HRID 464641ノート

反応式

HRID 464641 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 54008977HCID 54008977、化合物収率 93.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6fd33b4799be44808983ea32d19c9adb
出典データセット
uspto-grants-1985_10
特許番号
US04548929

反応ノート

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