2-Dimethylaminopyridine → 2,3-Dihydro-1h-inden-2-yl methanesulfonate

HRID 450726ノート

反応式

HRID 450726 の反応式
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[OH:10].C(N(C(C)C)CC)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].CN(C1C=CC=CN=1)C>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][S:21]([CH3:20])(=[O:23])=[O:22]

参加物

6

反応物 4

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 779362-IndanolHCID 81531Diisopropylethylamine

生成物 1

HCID 2552212,3-Dihydro-1h-inden-2-yl methanesulfonate収率 78%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-Indanol (20.00 g, 149.5 mmol) and diisopropylethylamine (21.2 g, 164 mmol) was stirred in dichloromethane (300 mL) at 0° C. Methanesulfonyl chloride (18.78 g, 164 mmol) and dimethylaminopyridine (1.80 g) were added simultaneously and stirring continued at room temperature for 18 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated. This was washed with NaHCO3 (sat) and with citric acid solution (5%) and dried over MgSO4. The filtered solution was concentrated and the resultant solid recrystallized from isopropanol-EtOH (3:1) to give off-white crystals (24.6 g, 78%).

後処理

  1. customSolution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customthe organic phase separated
  4. washThis was washed with NaHCO3 (sat) and with citric acid solution (5%)
  5. dry with materialdried over MgSO4
  6. concentrationThe filtered solution was concentrated
  7. customthe resultant solid recrystallized from isopropanol-EtOH (3:1)

出典と根拠

ORDレコード
ord-8a773c1aeae7433abb88a6f5b83d4413
出典データセット
uspto-grants-2013_07
特許番号
US08486984B2

反応ノート

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