Potassium bisulfate → SC-57666

HRID 1376523Notes

Reaction equation

HRID 1376523 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+].OS([O-])(=O)=O.[K+].CO.[CH2:35]1COCC1>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]([CH3:35])(=[O:25])=[O:22])=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 516920Potassium bisulfateHCID 106130741-[2-(4-Fluorophenyl)cyclopenten-1-yl]-4-(methylthio)benzeneHCID 21899815MeOH tetrahydrofuranHCID 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.KHSO4.K2SO4 ] in 23 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. 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 (CDCl3) δ 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, 2H), 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-2b7598771c97405ba2962d52b81c6911
Source dataset
uspto-grants-1997_09
Patent number
US05663180

Reaction notes

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