Tetrahydrofuran → 3-(5-Chloro-1,3-Dimethylpyrazole-4-sulfonyloxy)-5-methylphenol

HRID 442941노트

반응식

HRID 442941 반응식
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[Cl:11][C:12]1[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[C:13]=1[S:19](Cl)(=[O:21])=[O:20].O1CCCC1>C(OCC)C.C(=O)(O)[O-].[Na+]>[Cl:11][C:12]1[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[C:13]=1[S:19]([O:5][C:4]1[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=1)(=[O:20])=[O:21]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 27771265-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 3083941Resorcinol, 5-methyl-, monohydrate

생성물 1

HCID 545259863-(5-Chloro-1,3-Dimethylpyrazole-4-sulfonyloxy)-5-methylphenol수율 39.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
70 °C

실험 절차

A mixture of orcinol monohydrate (650 mg, 4.58 mmol) and 1.03 g (4.50 mmol) of 5-chloro-1,3-dimethylpyrazole-4-sulfonyl chloride in diethyl ether (20 mL) and saturated aqueous sodium bicarbonate (20 mL) was stirred overnight. To the reaction mixture was added 15 mL of tetrahydrofuran, and the reaction mixture was heated to 50° C. for 1 h and at 70° C. for 1 h. The reaction mixture was cooled to room temperature, extracted into ethyl acetate, dried (MgSO4), and purified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5 to 93:7)) to give the title compound (558 mg, 37% yield) as an oil. 1H-NMR (300 MHz, CDCl3) δ 6.91-6.92 (m, 1H), 6.57-6.61 (m, 1H), 6.41-6.50 (m, 1H), 5.93 (s, 1H), 3.82 (s, 3H), 2.29 (s, 3H), 2.25 (s, 3H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C12H13ClN2O4S: 316.9 (M+H). Found: 317.0.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted into ethyl acetate
  3. dry with materialdried (MgSO4)
  4. custompurified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5 to 93:7))

출처 및 근거

ORD 기록
ord-53380d6f4e09400caee3b6832bf2cfbb
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891909

반응 노트

불러오는 중…