2-Methoxypropene → HCID 21111959, compound

HRID 2167435Notes

Reaction equation

HRID 2167435 reaction equation
[CH3:1][O:2][C:3]([CH3:5])=[CH2:4].Cl[O-].[Na+].C([O-])(=O)C.[Na+].[Cl:14][C:15]1[C:24]([CH:25]=[N:26][OH:27])=[C:23]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]>C(Cl)Cl>[Cl:14][C:15]1[C:24]([C:25]2[CH2:4][C:3]([O:2][CH3:1])([CH3:5])[O:27][N:26]=2)=[C:23]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 83002-MethoxypropeneHCID 517045Sodium AcetateHCID 23665760Sodium HypochloriteHCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate

Product 1

HCID 21111959HCID 21111959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.3 g (102 mmol) of 2-methoxy-1-propene, 28 ml of sodium hypochlorite solution (12.5% strength) and a spatula-tip of sodium acetate were added successively to 10.0 g (34 mmol) of methyl 2-chloro-3-(hydroxyiminomethyl)-4-methylsulfonylbenzoate in 200 ml of methylene chloride. The mixture was stirred at room temperature for 12 hours, the solvent was removed and the residue was taken up in ethyl acetate, washed with water, dried and concentrated. The residue was chromatographed over silica gel (eluent: cyclohexane:ethyl acetate=3:2). This gave 5.8 g (47% of theory) of methyl 2-chloro-3-(5-methoxy-5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate.

Workup

  1. customthe solvent was removed
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (eluent: cyclohexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-e635833630404c29a5a62976049dcf5d
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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