4-Toluenesulfonyl chloride → 2-Isopropoxyethyl 4-methylbenzenesulfonate

HRID 546190ノート

反応式

HRID 546190 の反応式
[CH:1]([O:4][CH2:5][CH2:6][OH:7])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(Cl)Cl>[CH:1]([O:4][CH2:5][CH2:6][O:7][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 7996IsopropylethanediolHCID 8471Triethylamine

生成物 1

HCID 190994432-Isopropoxyethyl 4-methylbenzenesulfonate収率 81.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

In a round bottom flask was placed 2-isopropoxy-ethanol (700 mg, 6.72 mmol) dissolved in methylene chloride (15 mL) and cooled to 0° C. in an ice bath. To this solution was added triethylamine (1.2 mL, 8.7 mmol) and para-toluenesulfonyl chloride (1.54 g, 8.06 mmol). The resulting solution was then slowly allowed to warm to 25° C. and was stirred for 16 h. After this time, the reaction was transferred to a separatory funnel and washed with water (15 mL). The aqueous layer was then extracted with methylene chloride (2×20 mL). The organic layers were combined and then dried over sodium sulfate, filtered and concentrated in vacuo. Purification on an AnaLogix Intelliflash system (40 g column, 25% ethyl acetate/hexanes) afforded toluene-4-sulfonic acid 2-isopropoxy-ethyl ester (1.41 g, 81%).

後処理

  1. customIn a round bottom flask was placed
  2. temperatureto warm to 25° C.
  3. customAfter this time, the reaction was transferred to a separatory funnel
  4. washwashed with water (15 mL)
  5. extractionThe aqueous layer was then extracted with methylene chloride (2×20 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification on an AnaLogix Intelliflash system (40 g column, 25% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-a6d704c30e204863a2b2505cd26f12e5
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

反応ノート

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