Methyl acetoacetate → HCID 71255617, compound

HRID 1508329Notes

Reaction equation

HRID 1508329 reaction equation
[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([O:17]C)=[O:16])[N:11]=[N:10]2)[C:5]([F:8])=[CH:6][CH:7]=1.O=C(C)CC(OC)=O.C[O-].[Na+]>CO>[Cl:1][C:2]1[C:3]([F:19])=[C:4]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=[O:16])[N:11]=[N:10]2)[C:5]([F:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 10942334Sodium MethoxideHCID 71255683Methyl 1-(3-chloro-2,6-difluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 71255617HCID 71255617, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 1-(3-chloro-2,6-difluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate: The mixture of Intermediate 26A (1.16 g, 6.12 mmol), methyl 3-oxobutanoate (0.729 mL, 6.73 mmol), NaOMe (1.539 mL, 6.73 mmol), and MeOH (12 mL) in a microwave vial was stirred at 65° C. overnight. The reaction was concentrated and purified by silica gel chromatography to isolate the desired product (46 mg, 2%) as a yellow solid. MS(ESI) m/z: 287.8 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-00610aa886ac430f99fa9d19ed6698cb
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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