Sulfuryl chloride → Ethyl 2-chloro-3-oxohexanoate

HRID 1726369Notes

Reaction equation

HRID 1726369 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9])[CH3:2].S(Cl)([Cl:15])(=O)=O.C([O-])(O)=O.[Na+]>CCOCC>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([Cl:15])[C:6](=[O:10])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 238498Ethyl 3-oxohexanoateHCID 516892Sodium Bicarbonate

Product 1

HCID 11424094Ethyl 2-chloro-3-oxohexanoateYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

3-oxo-hexanoic acid ethyl ester (29.7 g, 188 mmol) was dissolved in Et2O (400 ml). The solution was cooled to 0° C., and sulfuryl chloride (22.6 ml, 282 mmol) was added dropwise. The solution gradually warmed to RT over 4 h. The solution was neutralized to pH 7 with a solution of aqueous saturated NaHCO3. The organic layer was separated, washed with brine, and dried over sodium sulfate. Evaporation under reduced pressure yielded 2-chloro-3-oxo-hexanoic acid ethyl ester (intermediate Id, 36 g, 100%). 1H-NMR (CDCl3, ppm): 0.95 d (3H); 1.35 d (3H); 1.58 m (2H); 2.7 t (2H); 4.28(d (2H); 4.78 s (1H).

Workup

  1. temperatureThe solution gradually warmed to RT over 4 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-68ddcb09fc6d43698e86e047fe97bbad
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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