Guaifenesin → HCID 19762939、化合物

HRID 249097

反応式

HRID 249097 の反応式
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][OH:9].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1.C1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:9][CH2:8][CH:7]([OH:10])[CH2:6][O:5][C:4]2[CH:11]=[CH:12][CH:13]=[CH:14][C:3]=2[O:2][CH3:1])(=[O:23])=[O:22])=[CH:17][CH:16]=1

参加物

5

反応物 2

HCID 3516GuaifenesinHCID 73974-Toluenesulfonyl chloride

生成物 1

HCID 19762939HCID 19762939、化合物収率 60.1%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 1049Pyridine溶媒

実験手順

A solution of 3-(2-methoxy-phenoxy)-propane-1,2-diol (4.7 g) in pyridine, cooled at 5°-10° C., is treated under stirring with a solution of p-toluensulphonylchloride (4.5 g) in benzene (70 ml). The reaction mixture is stirred overnight at room temperature, then it is washed with 2N HCl (3×100 ml) and with water, dried on Na2SO4 and evaporated to dryness in vacuum. The oily residue is purified by column chromatography (silica gel 230-400 mesh hexane/AcOEt=3/1) to yield 5 g of 3-(2-methoxy-phenoxy)-2-hydroxy-1-propyl p-toluensulphonate (oil, NMR (--CDCl3):δ=2,4 3H (s) CH3SO2 ; δ=3,75-4,4 5H (m) OCH3 +OCH2.

後処理

  1. additionis treated
  2. washit is washed with 2N HCl (3×100 ml) and with water
  3. customdried on Na2SO4
  4. customevaporated to dryness in vacuum
  5. customThe oily residue is purified by column chromatography (silica gel 230-400 mesh hexane/AcOEt=3/1)

出典と根拠

ORDレコード
ord-951d53943efa4613ae9d622148e68951
出典データセット
uspto-grants-1993_05
特許番号
US05212316

関連ノート

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