Sulfuryl chloride → HCID 10536831, compound

HRID 887975Notes

Reaction equation

HRID 887975 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH2:6]([O:8][C:9](=[O:18])[CH2:10][C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14])[CH3:7]>C(Cl)(Cl)Cl>[CH2:6]([O:8][C:9](=[O:18])[CH:10]([Cl:4])[C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14])[CH3:7]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 107026324,4-dimethyl-3-oxo-hex-5-enoic acid ethyl ester

Product 1

HCID 10536831HCID 10536831, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Sulfuryl chloride (0.84 ml, 10.4 mmol) was added to a cooled (0° solution of 4,4-dimethyl-3-oxo-hex-5-enoic acid ethyl ester (1.83 g, 9.93 mmol) in chloroform (7 ml). The resulting mixture was allowed to warm to room temperature and stir for 30 min, after which it was heated under reflux for 2 h. After cooling to room temperature the reaction mixture was diluted with chloroform, then was washed with sodium bicarbonate, water then brine. The organic phase was dried and evaporated to afford, as a brown oil, 2-chloro-4,4-dimethyl-3-oxo-hex-5-enoic acid ethyl ester (2.01 g, 93%). (Hayashi et al., J. Org. Chem., 65:8402-8405 (2000).

Workup

  1. temperatureafter which it was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. washwas washed with sodium bicarbonate, water
  5. customThe organic phase was dried
  6. customevaporated

Sources & evidence

ORD record
ord-195eb5caf0ad4268a34bc60ad758939c
Source dataset
uspto-grants-2012_08
Patent number
US08247552B2

Reaction notes

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