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

HRID 442941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442941
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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 545259863-(5-Chloro-1,3-Dimethylpyrazole-4-sulfonyloxy)-5-methylphenolAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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))

Quellen und Nachweise

ORD-Eintrag
ord-53380d6f4e09400caee3b6832bf2cfbb
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891909

Notizen zur Reaktion

Wird geladen…