Methanesulfonyl chloride → Cyclopent-3-en-1-yl methanesulfonate

HRID 2095658ノート

反応式

HRID 2095658 の反応式
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([O:6][S:8]([CH3:7])(=[O:10])=[O:9])[CH2:5][CH:4]=[CH:3][CH2:2]1

参加物

6

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 2814783-Cyclopenten-1-olHCID 516892Sodium Bicarbonate

生成物 1

HCID 12174535Cyclopent-3-en-1-yl methanesulfonate

試薬・触媒・溶媒 2

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

実験手順

To a solution of 3-cyclopentene-1-ol (9.00 g, 107 mmol) in dry methylene chloride (150 mL) was added TEA (23.0 mL, 160 mmol) followed by DMAP (100 mg). To this solution was added methanesulfonyl chloride (14.72 g, 128 mmol) at 10-20° C. slowly over 15 minutes and stirred overnight at room temperature. To the reaction mixture was added aqueous saturated NaHCO3 (50 mL) and stirred for 15 minutes at room temperature. The organic layer was separated, washed with water, followed by brine and dried over NaSO4. It was filtered and concentrated to give the title compound as an oil that was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3): δ=5.72 (s, 2H), 5.38 (mc, 1H), 3.00 (s, 3H), 2.81-2.61 (m, 4H).

後処理

  1. stirringstirred for 15 minutes at room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over NaSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c835edfa74f9458a9867ddd8c7f891e2
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

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