Sodium hydride → benzyl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-oxobutanoate

HRID 1696864Notes

Reaction equation

HRID 1696864 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[H-].[Na+].[CH2:10]([O:17][C:18](=[O:24])[CH:19](Br)[C:20](=[O:22])[CH3:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([CH:19]([C:20](=[O:22])[CH3:21])[C:18]([O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:24])[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1390011H-1,2,4-Triazole, 3,5-dimethyl-HCID 10978553Benzyl 2-bromo-3-oxobutanoate

Product 1

HCID 67274297benzyl 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a stirring solution of 3,5-dimethyl-1-H-[1,2,4]-triazole (0.502 g, 5.16 mmol) in THF (36.9 ml) was added NaH (0.199 g, 4.98 mmol). After stirring at RT for 10 mins 2-bromo-3-oxo-butyric acid benzyl ester (step 1) (1.0 g, 3.69 mmol) was added. The mixture was stirred at 40° C. for 30 mins and then allowed to cool to RT. The mixture was absorbed onto silica and purification by chromatography on silica eluting with 0-10% DCM/MeOH afforded the title compound as an orange oil; LC-MS Rt 1.95 mins; MS m/z 288.3 [M+H]+; Method LowpH_v001.

Workup

  1. additionwas added
  2. temperatureto cool to RT
  3. customThe mixture was absorbed onto silica and purification by chromatography on silica eluting with 0-10% DCM/MeOH

Sources & evidence

ORD record
ord-d46c8e8887e54e16bf03eb16ba026b0c
Source dataset
uspto-grants-2012_04
Patent number
US08163785B2

Reaction notes

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