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

HRID 37536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 37536
[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 ] 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-dimethylcyclopenten-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, R 11, 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-0a6f0361262e4fd889323b1c26c6a860
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420287

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