2-Cyanobenzenesulfonyl Chloride → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol Hydrochloride

HRID 1059461

反応式

HRID 1059461 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)(=[O:11])=[O:10])#[N:2].O.[C:22]1(O)C=C(C)C=[C:24]([OH:25])[CH:23]=1.C(C1C=CC=CC=1S([Cl:42])(=O)=O)#N>C([O-])(O)=O.[Na+].C(OCC)C.O>[ClH:42].[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:20][CH2:22][CH2:23][CH2:24][OH:25])(=[O:11])=[O:10])#[N:2]

参加物

7

反応物 3

HCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 227226433-(2-Cyanophenylsulfonyloxy)-5-methylphenol

生成物 1

HCID 186697053-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol Hydrochloride収率 57%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

3-(2-Cyanophenylsulfonyloxy)-5-methylphenol: Orcinol monohydrate (1.42 g, 10.0 mmol) and 2-cyanobenzenesulfonyl chloride (2.02 g, 10.0 mmol) were mixed in saturated NaHCO3 (30 mL) and diethyl ether (30 mL). The biphasic mixture was stirred vigorously at room temperature overnight. The reaction mixture was diluted with water (50 mL) and extracted into ethyl acetate (3×50 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.65 g, 57%). 1H-NMR (300 MHz, CDCl3) δ 8.07 (m, 1H), 7.94 (m, 1H), 7.75-7.80 (m, 2H), 6.57 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 5.69 (br s, 1H), 2.22 (s, 3H).

後処理

  1. extractionextracted into ethyl acetate (3×50 mL)
  2. washThe organic phase was washed with brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent in vacuo
  5. customthe residue was purified by flash column chromatography (dichloromethane to 5% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-b6531c9ea60c4c6a95928a78653eabc6
出典データセット
uspto-grants-2003_02
特許番号
US06518310B2

関連ノート

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