Sodium → Ethyl 2-chloroacetoacetate

HRID 1249633Notes

Reaction equation

HRID 1249633 reaction equation
[Na].[Cl:2][C:3]1[C:4](=[O:12])[O:5][C:6](C)([CH3:10])[O:7][C:8]=1[CH3:9]>C(O)C>[CH2:6]([O:5][C:4](=[O:12])[CH:3]([Cl:2])[C:8]([CH3:9])=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 135878355-Chloro-2,2,6-Trimethyl-1,3-Dioxin-4-One

Product 1

HCID 11858Ethyl 2-chloroacetoacetateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (0.3 g, 12 mmol) was added to 10 ml of ethanol, and then 5-chloro-2,2,6-trimethyl-4H-1,3-dioxin-4-one (1.76 g, 10 mmol) was added. The reaction was stirred one hour at 20° C., during which time the sodium dissolved. The reaction partitioned between ether and saturated ammonium chloride which had been acidified to pH ~2 with HCl. Evaporation of the ethereal layer, followed by distillation afforded 1.15 g (70%) of the title compound as a colorless liquid.

Workup

  1. dissolutiondissolved
  2. customThe reaction partitioned between ether and saturated ammonium chloride which
  3. customEvaporation of the ethereal layer
  4. distillationfollowed by distillation

Sources & evidence

ORD record
ord-e58bbc8af7a948fe9449eb8152afafa1
Source dataset
uspto-grants-1986_12
Patent number
US04633013

Reaction notes

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