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

HRID 28509

Reaction equation

HRID 28509 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 7a (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 7b (3.61 g, 48%) as a yellow oil. GCMS (EI) m/z 225 (M+-Cl16), 210 (M+-Cl-OMe).

Workup

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

Sources & evidence

ORD record
ord-16169f1d72cb421ba0df70e5d7011029
Source dataset
uspto-grants-2008_09
Patent number
US07419983B2

Linked notes

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