Pyridine → Cyclopent-3-en-1-yl methanesulfonate

HRID 222213ノート

反応式

HRID 222213 の反応式
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.N1C=CC=CC=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[CH3:13][S:14]([O:6][CH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1)(=[O:16])=[O:15]

参加物

5

反応物 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2 回HCID 2814783-Cyclopenten-1-ol

生成物 1

HCID 12174535Cyclopent-3-en-1-yl methanesulfonate収率 68.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

3-Cyclopentene-1-ol (0.500 g, 5.94 mmol) was stirred in DCM (95 mL). Pyridine (2.40 mL), N,N-dimethylaminopyridine (0.10 g, 1.00 mmol) and methanesulfonyl chloride (0.690 mL, 8.92 mmol) were added, and the reaction mixture was stirred at 35° C. for 4 h. N,N-Dimethylaminopyridine (0.14 g, 1.2 mmol) and methanesulfonyl chloride (0.69 mL, 8.92 mmol) were added, and the reaction was stirred overnight. TLC indicated complete conversion. The reaction mixture was cooled and concentrated. The residue was purified by silica gel chromatography, eluting with DCM, to afford the title compound as a clear oil (0.660 g, 68%).

後処理

  1. stirringthe reaction was stirred overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with DCM

出典と根拠

ORDレコード
ord-b980014275ae42bab0211f78cfe46a2a
出典データセット
uspto-grants-2012_06
特許番号
US08207177B2

反応ノート

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