1,3-Dichloroacetone → 3-Chloro-2-oxopropyl 3-methyl-3-[(2,4,6-trimethoxyphenyl)methylthio]butanoate

HRID 1357835Notes

Reaction equation

HRID 1357835 reaction equation
[CH3:1][C:2]([S:8][CH2:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=1[O:20][CH3:21])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].[Cl:27][CH2:28][C:29]([CH2:31]Cl)=[O:30]>CN(C=O)C>[CH3:7][C:2]([S:8][CH2:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=1[O:20][CH3:21])([CH3:1])[CH2:3][C:4]([O:6][CH2:31][C:29](=[O:30])[CH2:28][Cl:27])=[O:5]

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 154581393-Methyl-3(2,4,6-trimethoxyphenylmethylthio)butyric acid

Product 1

HCID 879910303-Chloro-2-oxopropyl 3-methyl-3-[(2,4,6-trimethoxyphenyl)methylthio]butanoateYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 3-methyl-3-[(2,4,6-trimethoxyphenyl)methylthio]butanoic acid (3 g, 9.54 mmol) and sodium bicarbonate (975 mg, 11.6 mmol) in DMF (30 mL) was added a solution of 1,3-dichloroacetone (4.23 g, 33.4 mmol) in DMF (15 mL) at 0° C. under nitrogen. The reaction mixture was allowed to warm to room temperature, and stirred for 48 hours. The residue after evaporation of the solvent was partitioned between EtOAc and H2O. The organic phase was washed with water and brine, dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel eluting with EtOAc:Hex (20-30%) to give the title compound as a yellow oil (2.19 g, 57%). 1H NMR (300 MHz, CDCl3) δ 6.12 (s, 2H), 4.87 (s, 2H), 4.21 (s, 2H), 3.86-3.80 (mult, 11H), 2.83 (s, 2H), 1.52 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 196.5, 170.1, 160.4, 158.6, 107.3, 90.7, 66.4, 55.8, 55.3, 46.3, 45.9, 43.8, 28.2, 20.9; mass spectrum (API-TIS) m/z 422 (M+NH4).

Workup

  1. customThe residue after evaporation of the solvent
  2. customwas partitioned between EtOAc and H2O
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-ef039b73429d467d9ed0a5d7fdfdc4da
Source dataset
uspto-grants-2003_07
Patent number
US06593347B2

Reaction notes

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