Methyl acetoacetate → HCID 18370748, compound

HRID 326423Notes

Reaction equation

HRID 326423 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C[O-].[Na+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Cl:18]>CO>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 960701-Bromo-5-chloropentaneHCID 10942334Sodium Methoxide

Product 1

HCID 18370748HCID 18370748, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
30 °C

Procedure

A mixture of methyl acetoacetate [VI-2] (127.7 g, 1.1 mol) and methanol (200 g) is heated to 30° C. Thereto is added dropwise 28.1 % solution of sodium methoxide in methanol (192 g, 1.0 mol), and the mixture is stirred for 1 hour. Thereto is added 1-bromo-5-chloropentane [V-1] (155.5 g, 0.838 mol), and the mixture is reacted at 70° C. for 2 hours. After completion of the reaction, the reaction mixture is concentrated under reduced pressure, and thereto is added toluene (500 g). The precipitated salt is removed by filtration. The toluene layer is washed with water and concentrated under reduced pressure to give methyl 7-chloro-2-(1-oxoethyl)heptanoate [II-2] (189.9 g, content; 88.7 %, yield; 91.2 %).

Workup

  1. customthe mixture is reacted at 70° C. for 2 hours
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. additionis added toluene (500 g)
  5. customThe precipitated salt is removed by filtration
  6. washThe toluene layer is washed with water
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e4ae54c20c24729982fd6fd2076ba32
Source dataset
uspto-grants-1993_12
Patent number
US05268501

Reaction notes

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