Pyridine → (S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

HRID 1358490ノート

反応式

HRID 1358490 の反応式
[CH3:1][C:2]1([CH3:10])[O:6][C@@H:5]([CH2:7][CH2:8][OH:9])[CH2:4][O:3]1.N1C=CC=CC=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:9][CH2:8][CH2:7][C@H:5]2[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 110518052-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

生成物 1

HCID 12486298(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate収率 67,699.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred mixture of 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (50.89 g, 0.348 mol) and pyridine (113 ml, 1.39 mol) in dichloromethane (500 ml) was added gradually p-toluenesulfonyl chloride (79.65 g, 0.418 mmol) at ice-bath temperature. After removal of ice-bath, the reaction mixture was stirred at ambient temperature overnight. The mixture was poured into ice-cooled 1N-HCl (400 ml) and the mixture was extracted with dichloromethane. The organic layer was washed with saturated NaHCO3 solution and brine, dried with MgSO4, and concentrated in vacuo. The residue was purified by silica gel (800 g) column chromatography eluting with toluene/ethyl acetate (50:1 to 10:1) to give 2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl p-toluenesulfonate (85.0 g, 81.3%) as an oil.

後処理

  1. customAfter removal of ice-bath
  2. additionThe mixture was poured into ice-
  3. temperaturecooled 1N-HCl (400 ml)
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe organic layer was washed with saturated NaHCO3 solution and brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel (800 g) column chromatography
  9. washeluting with toluene/ethyl acetate (50:1 to 10:1)

出典と根拠

ORDレコード
ord-c8b3871e91374389b9daf7dbd1ecc0e5
出典データセット
uspto-grants-2003_07
特許番号
US06596738B1

反応ノート

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