4-Toluenesulfonyl chloride → 1-(2-Methyl-1,3-dioxolan-2-yl)-1-p-toluenesulfonyloxymethylcyclopropane

HRID 1613556ノート

反応式

HRID 1613556 の反応式
[OH:1][CH2:2][C:3]1([C:6]2([CH3:11])[O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:11][C:6]1([C:3]2([CH2:2][O:1][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH2:4][CH2:5]2)[O:7][CH2:8][CH2:9][O:10]1

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22042312[1-(2-Methyl-1,3-dioxolan-2-yl)cyclopropyl]methanol

生成物 1

HCID 536511091-(2-Methyl-1,3-dioxolan-2-yl)-1-p-toluenesulfonyloxymethylcyclopropane

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred and ice-cooled solution of 3 (5.0 g, 31.6 mmol), N,N-dimethyl-4-aminopyridine (386 mg, 8.16 mmol) and triethylamine (22 mL, 158 mmol) in dichloromethane (25 mL) was added p-toluenesulfonyl chloride (7.23 g, 37.9 mmol) portionwise and the mixture was stirred in a cold room at 4° C. overnight. The mixture was poured into ice water, and the organic layer was separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water and brine, and dried over sodium sulfate. Filtration and concentration gave 16.70 g of crude 4, as a pale yellow oil, which was used in the next step without further purification.

後処理

  1. stirringthe mixture was stirred in a cold room at 4° C. overnight
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration
  7. customgave 16.70 g of crude 4
  8. customas a pale yellow oil, which was used in the next step without further purification

出典と根拠

ORDレコード
ord-a9cf13ab579f4170aa24ba0d12a63f5b
出典データセット
uspto-grants-1993_03
特許番号
US05194431

反応ノート

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