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Water → 2,3-Dicarbomethoxycyclobutyl phenyl sulfone

HRID 5973
Notes
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Reaction equation

HRID 5973 reaction equation
[C:1]1([S:7][CH:8]2[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]2[C:16]([O:18][CH3:19])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:20]OS([O-])=O.[K+].[K+].S(=O)(=O)([O-])[O-].[K+].S([O-])(OO)(=O)=O.[K+].[OH2:40]>CO.ClC(Cl)C>[C:1]1([S:7]([CH:8]2[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]2[C:16]([O:18][CH3:19])=[O:17])(=[O:20])=[O:40])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 962Water2×HCID 24507Potassium SulfateHCID 19794294Dimethyl 3-(phenylthio)cyclobutane-1,2-dicarboxylateHCID 23707502Potassium hydroxy sulfiteHCID 23712892Potassium peroxymonosulfate

Product 1

HCID 197942682,3-Dicarbomethoxycyclobutyl phenyl sulfone
Yield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a vigorously stirred solution of 1.05 g (3.75 mmol) of dimethyl 3-(phenylthio)cyclobutane-1,2-dicarboxylate from Step A in 20 mL of methanol, was added slowly a suspension of 3.46 g (11.25 mmol) of OXONE (a commercially available mixture of sulfuric acid potassium salt and potassium hydrogen peroxymonosulfate) in 20 mL of water. The resultant cloudy suspension was stirred for 0.5 h then diluted with 50 mL of water and 100 mL of 1,2=dichloroethane. The phases were allowed to separate and the aqueous phase was extracted with 20 mL of 1,2-dichloroethane. The combined organic layers were washed with 2×50 mL of dilute aqueous sodium bicarbonate solution, 2×50 mL of water and 50 mL of brine, dried over anhydrous magnesium sulfate and concentrated to give 1.10 g (94% yield) of the title compound as a viscous oil; EI-MS, m/e (relative intensity): 281 (M+ --OCH3, 9), 171 (100), 139 (24), 111 (47); 1H NMR (CDCl3) δ2.48 (m, 1H), 2.76 (m, 1H), 3.23 (q, 1H), 3.52 (s, 3H), 3.74 (s, 3H), 3.80 (m, 1H), 3.92 (q, 1H), 7.58 (m, 2H), 7.68 (m, 1H), 7.89 (m, 2H).

Workup

  1. customto separate
  2. extractionthe aqueous phase was extracted with 20 mL of 1,2-dichloroethane
  3. washThe combined organic layers were washed with 2×50 mL of dilute aqueous sodium bicarbonate solution, 2×50 mL of water and 50 mL of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-70dbc0e828674b098de600e6c942e203
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05246931

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes