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

HRID 442941ノート

反応式

HRID 442941 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-53380d6f4e09400caee3b6832bf2cfbb
出典データセット
uspto-grants-1999_04
特許番号
US05891909

反応ノート

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