Water → HCID 12629501, compound

HRID 424380Notes

Reaction equation

HRID 424380 reaction equation
[C:1]([S:5][CH2:6][O:7][CH3:8])([CH3:4])([CH3:3])[CH3:2].S([O-])(O[O-])(=O)=[O:10].[K+].[K+].[OH2:17]>CO>[C:1]([S:5]([CH2:6][O:7][CH3:8])(=[O:10])=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 10313463Potassium peroxymonosulphateHCID 12629500HCID 12629500, compound

Product 1

HCID 12629501HCID 12629501, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methoxymethyl t-butyl sulphide XIV(ii) (2.68 g, 0.020 mol) in MeOH (80 mL) was added a solution of potassium peroxymonosulfate (2 KHSO5 KHSO4 K2SO4, Oxone®) (36.8 g, 0.060 mol) in water (80 mL) at 0° C. The resulting cloudy solution was warmed to room temperature and then stirred overnight. The mixture was diluted with water (30 mL), extracted with EtOAc (3×70 mL), washed with brine, dried over MgSO4, concentrated in vacuo, and then purified by column chromatography (25% EtOAc/hexanes) to give 3.05 g (92%) of Methoxymethyl t-butyl sulfone XII(iii) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 4.50 (s, 2H), 3.63 (s, 3H), 1.38 (s, 9H); 13NMR (100 MHz, CDCl3) δ 83.19, 60.84, 59.61, 23.32.

Workup

  1. extractionextracted with EtOAc (3×70 mL)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d76c67e7f3274a72bbe9f8aba5e954f6
Source dataset
uspto-grants-2012_01
Patent number
US08106035B2

Reaction notes

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