Water → Methyl 4-(3-chloropropylsulfonyl)benzoate

HRID 713092ノート

反応式

HRID 713092 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[OH2:16].[OH:17]OS([O-])=O.[K+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)(=[O:17])=[O:16]

参加物

5

反応物 3

HCID 962WaterHCID 13749599Methyl 4-(3-chloropropylthio)benzoateHCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 68290846Methyl 4-(3-chloropropylsulfonyl)benzoate収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl 4-(3-chloropropylsulfanyl)benzoate (1.84 g, 7.52 mmol) was dissolved in methanol (46 mL), followed by the addition of water (4.6 mL) and Oxone (4.62 g, 7.52 mmol). The reaction mixture was stirred at room temperature for 14 h. The reaction mixture was filtered and the solvent removed in vacuo. The resulting solid was dissolved in dichloromethane and washed with water (2×10 mL). The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo to yield methyl 4-(3-chloropropylsulfonyl)benzoate (1.89 g, 91%) as a viscous liquid. ESI-MS m/z calc. 276.0. found 277.1 (M+1)+; Retention time: 1.36 minutes (3 min run). 1H NMR (400 MHz, DMSO-d6) δ 8.21 (d, J=8.3 Hz, 2H), 8.07 (d, J=8.3 Hz, 2H), 3.92 (s, 3H), 3.73-3.46 (m, 4H), 2.21-1.79 (m, 2H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed in vacuo
  3. dissolutionThe resulting solid was dissolved in dichloromethane
  4. washwashed with water (2×10 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-34c742a2415c42448f59c1db5d791cbc
出典データセット
uspto-grants-2015_11
特許番号
US09181273B2

反応ノート

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