Ethyl Acetoacetate → Ethyl 2-acetyl-7-chloroheptanoate

HRID 326421Notes

Reaction equation

HRID 326421 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[Cl:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 11430Potassium Carbonate2×HCID 960701-Bromo-5-chloropentane

Product 1

HCID 11746602Ethyl 2-acetyl-7-chloroheptanoateYield 72.6%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of ethyl acetoacetate [VI-1] (260.2 g, 2.0 mol), methyl isobutyl ketone 300 9) and 1-bromo-5-chloropentane [V-1] (311.0 g, 1.68 mol) is heated to 80°-90° C. Thereto is added anhydrous potassium carbonate (300 g), and the mixture is reacted at 80°-90° C. for 12 hours. To the reaction mixture is further added potassium carbonate (341.4 g), and the mixture is reacted for additional 6 hours. After completion of the reaction, the mixture is filtered, and the methyl isobutyl ketone layer is washed with water and concentrated under reduced pressure. The residue (398.6 g) contains ethyl 7-chloro-2-(1-oxoethyl)-heptanoate (content; 70.8 %, yield; 72.6 %), which is purified by column chromatography to give pure ethyl 7-chloro-2-(1-oxoethyl)heptanoate [II-1].

Workup

  1. temperatureis heated to 80°-90° C
  2. customthe mixture is reacted at 80°-90° C. for 12 hours
  3. customthe mixture is reacted for additional 6 hours
  4. customAfter completion of the reaction
  5. filtrationthe mixture is filtered
  6. washthe methyl isobutyl ketone layer is washed with water
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0d94d55e6284a94846557a1213e796b
Source dataset
uspto-grants-1993_12
Patent number
US05268501

Reaction notes

Loading…