4-Toluenesulfonyl chloride → 4-(4-Bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate

HRID 338531ノート

反応式

HRID 338531 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])=[CH:6][CH:5]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>O1CCCC1>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([Br:3])=[CH:17][CH:16]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 794507012-(2-(4-Bromophenoxy)ethyl)propane-1,3-diol

生成物 1

HCID 866988534-(4-Bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate収率 46%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of NaH (0.11 g, 4.58 mmol) in anhydrous tetrahydrofuran (10 mL) was added a solution of 2-(2-(4-bromophenoxy)ethyl)propane-1,3-diol (0.63 g, 2.29 mmol) in anhydrous tetrahydrofuran (10 mL) dropwise. The reaction mixture was stirred at room temperature for 30 minutes. Then, tosyl chloride (0.44 g, 2.3 mmol) was added in portions. The reaction mixture was then stirred at room temperature for 2 hours. The reaction mixture was carefully quenched with water and extracted with ethyl acetate (4×30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (0-35% ethyl acetate/petroleum ether) to afford the title compound (0.45 g, 46%) as white solid. 1H NMR (400 MHz, CDCl3) ppm 7.80 (d, 2H), 7.40-7.30 (m, 4H), 6.71 (d, 2H), 4.21-4.09 (m, 2H), 4.00-3.90 (m, 2H), 3.74-3.62 (m, 2H), 2.45 (s, 3H), 2.14 (m, 1H), 1.89-1.74 (m, 3H).

後処理

  1. stirringThe reaction mixture was then stirred at room temperature for 2 hours
  2. customThe reaction mixture was carefully quenched with water
  3. extractionextracted with ethyl acetate (4×30 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product, which
  8. customwas purified by flash chromatography (0-35% ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-872da749a3c1423e8179cc4c47e2a8e5
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

反応ノート

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