Ethyl Acetoacetate → Ethyl 2-acetyl-7-chloroheptanoate

HRID 326422Notes

Reaction equation

HRID 326422 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+]>CCCCCCC>[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 CarbonateHCID 960701-Bromo-5-chloropentane

Product 1

HCID 11746602Ethyl 2-acetyl-7-chloroheptanoateYield 176%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl acetoacetate [VI-1] (109.3 g), n-heptane (100 g) and 1-bromo-5-chloropentane [V-1] (185.5 g) is heated to 90° C. Thereto is added anhydrous potassium carbonate (193.5 g) in portions, and the mixture is stirred with heating at 100° C. for 14 hours. The mixture is filtered with suction, and the residue is washed with n-heptane. The n-heptane layers (i.e. the above filtrate and washing liquid) are combined to give a solution (347 g) of crude ethyl 7-chloro-2-(1-oxoethyl)heptanoate [II-1] in n-heptane (content of the heptanoate; 44.3 %).

Workup

  1. temperaturewith heating at 100° C. for 14 hours
  2. filtrationThe mixture is filtered with suction
  3. washthe residue is washed with n-heptane
  4. washThe n-heptane layers (i.e. the above filtrate and washing liquid)

Sources & evidence

ORD record
ord-975e961bbbf24d4d9cc1df666c3bb6c6
Source dataset
uspto-grants-1993_12
Patent number
US05268501

Reaction notes

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