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

HRID 442941Notes

Reaction equation

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]

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-53380d6f4e09400caee3b6832bf2cfbb
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891909

Reaction notes

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