Methyl 2-chloroacetoacetate → HCID 59457502, compound

HRID 1710737Notes

Reaction equation

HRID 1710737 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1.Cl[CH:16]([C:21](=O)[CH3:22])[C:17]([O:19][CH3:20])=[O:18]>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]2[O:11][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:21]([CH3:22])[N:12]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 107332Methyl 2-chloroacetoacetateHCID 144071764-(3-Chloropropoxy)benzamide

Product 1

HCID 59457502HCID 59457502, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(3-chloro-propoxy)-benzamide (0.5 g, 2.34 mmol, 1 eq) and methyl 2-chloro-3-oxobutanoate (0.7 ml, 5.62 mmol, 2.4 eq) in ethanol (5 ml) is heated at 110° C. in a sealed tube for 24 h. The mixture is concentrated, taken up in dichloromethane and washed with water. The organic phase is dried over magnesium sulfate and concentrated. The residue is purified by chromatography over silicagel (eluent: dichloromethane) to afford 0.7 g of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-oxazole-5-carboxylate ax60 as a pale yellow solid.

Workup

  1. concentrationThe mixture is concentrated
  2. washwashed with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography over silicagel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-7094c3aecd8e46e8a30bf861a293518b
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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