3,4-dihydro-2H-pyran → HCID 54008977、化合物

HRID 2295287ノート

反応式

HRID 2295287 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.CC1C=CC(S(O)(=O)=O)=CC=1.O.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 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 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 ptoluenesulfonic 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 etherhexane 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-4ef8cb3388ce4452a3396e5414b3a905
出典データセット
uspto-grants-1984_01
特許番号
US04424213

反応ノート

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