Methanol → SC-57666

HRID 2225992Notes

Reaction equation

HRID 2225992 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:13]2[CH:18]=[CH:17][C:16](SC)=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.O[O:22][S:23]([O-:25])=O.[K+].[CH3:27]O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:13]2[CH:14]=[CH:15][C:16]([S:23]([CH3:27])(=[O:25])=[O:22])=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 106130741-[2-(4-Fluorophenyl)cyclopenten-1-yl]-4-(methylthio)benzeneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 443373SC-57666Yield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.5 g (5. mmol) of 1-[2-(4-fluorophenyl) cyclopenten-1-yl]-4-(methylthio)benzene (Step 3) in 46 mL of methanol/thf (1:1) was slowly treated with 5.2 g (8.4 mmol) of Oxone® [2 KHSO5.K2SO4 ] in 23 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. Recrystallization from ethyl acetate/hexane provided 960 mg (54%) of 1-[2-(4-fluorophenyl) cyclopenten-1-yl]-4- (methylsulfonyl)benzene (41 in Synthetic Scheme X when R5 =SO2CH3, R10 =F, and R1, R2, R3, R4, R6, R7, R8, R9, R11, and R12 =H) as a colorless solid: mp 138°-139° C.; NMR (CDCl 3) d 2.09 (m, J=7 Hz, 2H) , 2.91 (t, J=7 Hz, 4H) , 3.04 (s, 3H) , 6.88-6.96 (m, 2H) , 7.06-7.14 (m, 2H) , 7.32 (d, J=8 Hz, 2 H), 7.76 (d, J=8 Hz, 2H). MS (EI) m/e (rel intensity) 316 (100) , 237 (41) , 161 (13); HRMS. Calc'd for C18H17FO2S: 316.0933. Found: 316.0943. Anal. Calc'd for C18H17FO2S: C, 68.33; H, 5.42; F, 6.00; S, 10.13 . Found: C, 68.08; H, 5.45; F, 6.42; S, 9.98.

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. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-37e26fb1e19c48c08b49a99061c19a29
Source dataset
uspto-grants-1994_09
Patent number
US05344991

Reaction notes

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