Methyl acetoacetate → Methyl 3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylate

HRID 2276401Notes

Reaction equation

HRID 2276401 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](Cl)=[N:5][OH:6].[CH3:12][O:13][C:14](=[O:19])[CH2:15][C:16]([CH3:18])=O.C[O-].[Na+]>CO>[CH3:12][O:13][C:14]([C:15]1[C:4]([C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[Cl:1])=[N:5][O:6][C:16]=1[CH3:18])=[O:19]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 380973329568-74-9HCID 10942334Sodium Methoxide

Product 1

HCID 2763469Methyl 3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner as described in Preparation Example 17, by using methanol (160 mL), 2-chloro-N-hydroxybenzimidoylchloride (8.0 g, 42.10 mmol), methylacetoacetate (9.78 g, 84.20 mmol) and sodium methoxide (6.83 g, 126.30 mmol), a white solid required compound (6.32 g, 25.11 mmol, 60%) was obtained.

Workup

  1. customIn a similar manner as described in Preparation Example 17

Sources & evidence

ORD record
ord-77ce7e51f2434226a1f47838a503bed1
Source dataset
uspto-grants-2015_09
Patent number
US09132126B2

Reaction notes

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