Sulfuryl chloride → ethyl 3-chloro-2,4-dioxopentanoate

HRID 1870494Notes

Reaction equation

HRID 1870494 reaction equation
S(Cl)([Cl:4])(=O)=O.[O:6]=[C:7]([CH2:13][C:14](=[O:16])[CH3:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(Cl)Cl>[Cl:4][CH:13]([C:14](=[O:16])[CH3:15])[C:7](=[O:6])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 69208Ethyl 2,4-dioxovalerate

Product 1

HCID 3006755ethyl 3-chloro-2,4-dioxopentanoateYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of sulfuryl chloride (7.08 g, 52 mmol) in 15 mL of CH2Cl2 was added dropwise to a solution of ethyl 2,4-dioxovalerate (7.91 g, 40 mmol) in 125 ml of CH2Cl2 at room temperature. After three hours TLC analysis indicated that all of the starting material had been consumed. The reaction mixture was washed with H2O (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 7.84 g (81% yield) of the desired product as and orange oil: 1H NMR (CDCl3) 67 14.4 (bs, 1H), 5.4 (s, 1H), 4.4-4.3 (m, 4H), 2.5 (s, 3H), 2.4 (s, 3H), 1.4-1.35 (s, 6H) for a 1:1 mixture of tautomers.

Workup

  1. customhad been consumed
  2. washThe reaction mixture was washed with H2O (2×100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9a4d8d0e71d48f89f19c091c61bca21
Source dataset
uspto-grants-2000_08
Patent number
US06096898

Reaction notes

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