Potassium bisulfate → 1-[2-(4-Fluorophenyl)-4,4-dimethyl-1-cyclopentenyl]-4-methylsulfonylbenzene

HRID 2226008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226008
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18](SC)=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.O[O:24][S:25]([O-:27])=O.[K+].OS([O-])(=O)=O.[K+].[CH3:35]O.O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=2[C:15]2[CH:16]=[CH:17][C:18]([S:25]([CH3:35])(=[O:27])=[O:24])=[CH:19][CH:20]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 516920Potassium bisulfateHCID 104482441-[2-(4-Fluorophenyl)-4,4-dimethylcyclopenten-1-yl]-4-(methylthio)benzeneHCID 22242641Methanol--water (1/1)HCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 98410791-[2-(4-Fluorophenyl)-4,4-dimethyl-1-cyclopentenyl]-4-methylsulfonylbenzeneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 120 mg (0.39 mmol) of 1-[2-(4-fluorophenyl)-4,4-dimethylcyclopenten-1-yl]-4-(methylthio)benzene (Step 9 ) in 3 mL of methanol/water (1:1) was slowly treated with 470 mg (0.76 mmol) of Oxone® [2 KHSO5.KHSO4.K2SO4 ] in 2 mL of water. After stirring for 4 h, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed with water and brine, dried (MgSO4), and reconcentrated. Purification by silica gel chromatography (MPLC) with hexane/ethyl acetate (5:1) and subsequent lyophilization from acetonitrile/water (1:1) gave 50 mg (38%) of 1-[2-(4-fluorophenyl)-4,4-dimethyl cyclopenten-1-yl]-4-(methylsulfonyl)benzene (41 in Synthetic Scheme X when R1 and R2 =CH3, R5 =F, R10 =SO2CH3, R3, R4, R6, R7, R8, R9, R11, and R12 =H) as a colorless solid: NMR (CDCl3) d 1.24 (s, 6H) , 2.71 (s, 4H), 3.4 (s, 3H), 6.92 (t, J=8 Hz, 2H), 7.05-7.12 (m, 2H) , 7.30 (d, J=9 Hz, 2H) , 7.75 (d, J=9 Hz, 3H); MS (EI) m/e (rel intensity) 344 (100) , 329 (33) , 250 (18) , 235 (20) , 109 (35) , 69 (44); HRMS. Calc'd for C20H21FO2S: 344.1246. Found: 344.1272.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customPurification by silica gel chromatography (MPLC) with hexane/ethyl acetate (5:1) and subsequent lyophilization from acetonitrile/water (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-86f2f913179c4df8b6ad6cc462111eae
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344991

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