Methyl (methylsulfinyl)methyl sulfide → 2-Chloro-1-methoxy-3-[2-(methylsulfanyl)-2-(methylsulfinyl)vinyl]benzene

HRID 2054527Notes

Reaction equation

HRID 2054527 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][S:13][CH2:14][S:15]([CH3:17])=[O:16]>C1COCC1>[Cl:1][C:2]1[C:3]([CH:4]=[C:14]([S:13][CH3:12])[S:15]([CH3:17])=[O:16])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 125756952-Chloro-3-methoxybenzaldehyde

Product 1

HCID 865965082-Chloro-1-methoxy-3-[2-(methylsulfanyl)-2-(methylsulfinyl)vinyl]benzeneYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-3-methoxybenzaldehyde 3a (4.65 g, 27.3 mmol) and methyl (methylthio)methyl sulfoxide (4.3 mL, 43.9 mmol) in THF (25 mL) was added a 40% methanolic solution of Triton B (6.2 mL, 13.6 mmol) and the resulting solution was refluxed for 16 hours. After THF was removed, the residue was taken up in ethyl acetate, washed with 1 N HCl, H2O, and brine, then was dried over Na2SO4, and concentrated. Purification by column chromatography on silica gel with dichloromethane afforded 2-chloro-1-methoxy-3-[2-(methylsulfanyl)-2-(methylsulfinyl)vinyl]benzene 3b (3.61 g, 48%) as a yellow oil. GCMS (EI) m/z 225 (M+-Cl-16), 210 (M+-Cl-OMe).

Workup

  1. temperaturethe resulting solution was refluxed for 16 hours
  2. customAfter THF was removed
  3. washwashed with 1 N HCl, H2O, and brine
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-930fb3b83d9541149860a6b9c286cc0a
Source dataset
uspto-grants-2008_02
Patent number
US07329669B2

Reaction notes

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