Ethyl Acetate → Ethyl 2-chloro-3-cyclohexyl-3-oxopropanoate

HRID 1530017Notes

Reaction equation

HRID 1530017 reaction equation
[CH:1]1([C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:18])(=O)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(OCC)C>[Cl:18][CH:8]([C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 266327Ethyl 3-cyclohexyl-3-oxopropanoateHCID 516892Sodium Bicarbonate

Product 1

HCID 86649589Ethyl 2-chloro-3-cyclohexyl-3-oxopropanoateYield 74.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 3-cyclohexyl-3-oxopropanoate (1.0 g, 5.0 mmol) in diethyl ether (15 mL) was added sulfuryl chloride (750 mg, 5.5 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium bicarbonate solution (150 mL) and ethyl acetate (150 mL) were added to the reaction solution, and the mixture was stirred for 30 min. The organic layer was washed with saturated brine (10 mL) and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure to give the title compound (870 mg, 60%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washThe organic layer was washed with saturated brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationthe insoluble material was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a7f0c4bd4af44ab39d50599f7983ea55
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

Loading…