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

HRID 36965Notes

Reaction equation

HRID 36965 reaction equation
[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]([S:21][CH3:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[OH:23]OS([O-])=O.[K+].OS([O-])(=O)=O.[K+].[OH2:35]>CO.O>[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:16]=[CH:17][C:18]([S:21]([CH3:22])(=[O:23])=[O:35])=[CH:19][CH:20]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 104482441-[2-(4-Fluorophenyl)-4,4-dimethylcyclopenten-1-yl]-4-(methylthio)benzeneHCID 23707502Potassium hydroxy sulfite

Product 1

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

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

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 hours, 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, RS=F, R10 =SO2CH3, and R3, R4, R6, R7, R8, R9, R11 and R12=H) as a colorless solid: NMR (CDCl3) δ1.24 (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.

Workup

  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)

Sources & evidence

ORD record
ord-c7daf79554c0457da16dde866a4e6ef1
Source dataset
uspto-grants-1995_05
Patent number
US05418254

Reaction notes

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