Methanol → 2-chloro-1-((E)-2-methanesulfinyl-2-methylsulfanyl-vinyl)-3-methoxy-benzene

HRID 1773976Notes

Reaction equation

HRID 1773976 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.C[CH:13]([S:17][CH:18](S(C)=O)C)[S:14]([CH3:16])=[O:15].CO>C1COCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[C:13](/[S:14]([CH3:16])=[O:15])\[S:17][CH3:18]

Participants

6

Reactant 3

HCID 887MethanolHCID 125756952-Chloro-3-methoxybenzaldehydeHCID 54140058Methylmethylsulfinylmethyl sulfide

Product 1

HCID 220378702-chloro-1-((E)-2-methanesulfinyl-2-methylsulfanyl-vinyl)-3-methoxy-benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 66854Benzyltrimethylammonium hydroxideSolvent

Procedure

To a solution of 2-chloro-3-methoxybenzaldehyde (1.74 g, 10.0 mmol, 1.0 eq.) and methyl(methylsulfinyl)methyl sulfide (1.72 mL, 16.1 mmol, 1.6 eq.) in THF (9 mL), benzyltrimethylammonium hydroxide solution in methanol (2.3 mL, 10.0 mmol, 1.0 eq.) was added. The resulting solution was refluxed for 18 hours. The solvent was removed in vacuo. The residue was taken up in AcOEt and washed with 1M aq. HCl soln., water, and sat. aq. NaCl soln. The org. layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane+20% AcOEt to Heptane+65% AcOEt) to yield 2-chloro-1-((E)-2-methanesulfinyl-2-methylsulfanyl-vinyl)-3-methoxy-benzene as a pale orange oil.

Workup

  1. temperatureThe resulting solution was refluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. washwashed with 1M aq. HCl soln
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane+20% AcOEt to Heptane+65% AcOEt)

Sources & evidence

ORD record
ord-8179540632984d578b36485f7a7fcce1
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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