Ethyl Acetate → Ethanone, 1-[2-methoxy-4-(methylthio)phenyl]-

HRID 452443Notes

Reaction equation

HRID 452443 reaction equation
[CH3:1][S-:2].[Na+].F[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[C:7]([O:14][CH3:15])[CH:6]=1.CCOC(C)=O>CN(C=O)C>[CH3:15][O:14][C:7]1[CH:6]=[C:5]([S:2][CH3:1])[CH:10]=[CH:9][C:8]=1[C:11](=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1428871-(4-Fluoro-2-methoxyphenyl)ethan-1-oneHCID 4378561Sodium methanethiolate

Product 1

HCID 13578023Ethanone, 1-[2-methoxy-4-(methylthio)phenyl]-Yield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-15 °C

Procedure

Sodium thiomethoxide (3.35 g, 47.8 mmol) was dissolved in dry DMF (35 ml) under a blanket of nitrogen. The solution was cooled to −15° C. and 1-(4-fluoro-2-methoxyphenyl)ethanone (6.7 g, 39.8 mmol) was added in portions. After 10 min at −15° C. the reaction mixture was brought to 0° C. for 1.5 h. EtOAc was added and the organic phase was washed three times with aqueous HCl (10%), dried (Na2SO4) and evaporated under reduced pressure to dryness. Purification by flash column chromatography (isooctane/EtOAc 4:1) gave the pure title compound (6.3 g, 81%). MS m/z (rel. intensity, 70 eV) 196 (M+, 37), 182 (11), 181 (bp), 166 (7), 138 (10).

Workup

  1. washthe organic phase was washed three times with aqueous HCl (10%)
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure to dryness
  4. customPurification by flash column chromatography (isooctane/EtOAc 4:1)

Sources & evidence

ORD record
ord-a6c22a7eb6bf446481e14a8ec9052a3b
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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