Sulfuryl chloride → HCID 10536831, compound

HRID 1917445Notes

Reaction equation

HRID 1917445 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-818ffa86c3e0420a973a4f5f19dc6522
Source dataset
uspto-grants-2013_12
Patent number
US08618292B2

Reaction notes

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