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

HRID 1059461

반응식

HRID 1059461 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b6531c9ea60c4c6a95928a78653eabc6
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518310B2

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