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Water → (-)-1-Benzoyl-2,3-di-p-toluenesulfonyl glycerol

HRID 1074650
ノート
印刷プレビュー

反応式

HRID 1074650 の反応式
[C:1]([O:9][CH2:10][CH:11]([CH2:13][OH:14])[OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[OH2:26].C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([O:9][CH2:10][CH:11]([CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:22])=[O:26])[O:12][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962Water2 回HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 1379111-Monobenzoylglycerol

生成物 1

HCID 12914086(-)-1-Benzoyl-2,3-di-p-toluenesulfonyl glycerol収率 72%

試薬・触媒・溶媒 1

HCID 1049Pyridine
溶媒

反応条件

温度
0 °C

実験手順

To a solution of 35.5 g (181 mmol) of (-)-1-benzoyl glycerol (G) in 250 ml of dry pyridine at 0° C. is added 83 g (433 mmol) of p-toluenesulfonyl chloride. The mixture is stirred at 0° C. for 15 minutes and then stored in a refrigerator for 144 hours. After cooling the reaction mixture to 0° C., 10 ml of water are added, the mixture is stirred for 10 minutes, and then poured into excess water. The aqueous solution is separated from the gummy product, and extracted with chloroform. The gummy residue is dissolved in chloroform and the combined chloroform solution is washed sequentially with 3 N hydrochloric acid, water, 5% sodium bicarbonate solution, and water. The chloroform solution is dried over Na2SO4 and concentrated under reduced pressure to obtain a solid which, upon recrystallization from absolute ethanol, gives 65.5 g (130 mmol, 72%) of (-)-1-benzoyl-2,3-di-p-toluenesulfonyl glycerol (see Formula (H) in Scheme 2), m.p. 105°-106° C. [α]D2° -22.7 (c, 5.92, CHCl3). 1H NMR (CDCl3) δ8-7 (m, 13H); 4.9 (m, 1H); 4.45 (d, 2H, J=6 Hz); 4.35 (d, 2H, J=5 Hz); 2.42 (s, 3H); 2.38 (s, 3H). 13C NMR (CDCl3) 165.162, 145.136, 133.108, 132.466, 131.649, 129.430, 128.671, 128.087, 127.678, 75.306, 66.899, 61.994, 21.591 ppm.

後処理

  1. waitstored in a refrigerator for 144 hours
  2. temperatureAfter cooling the reaction mixture to 0° C.
  3. stirringthe mixture is stirred for 10 minutes
  4. customThe aqueous solution is separated from the gummy product
  5. extractionextracted with chloroform
  6. dissolutionThe gummy residue is dissolved in chloroform
  7. washthe combined chloroform solution is washed sequentially with 3 N hydrochloric acid, water, 5% sodium bicarbonate solution, and water
  8. dry with materialThe chloroform solution is dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto obtain a solid which
  11. customupon recrystallization from absolute ethanol

出典と根拠

ORDレコード
ord-8ffdabc5f56d4d86a9f7b99d1f9f11ce
出典データセット
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04393240

反応ノート

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