1-tert-butyl-1H-pyrazole-4-carboxylic acid methoxy-methyl-amide → 1460286-48-9

HRID 2272970Notes

Reaction equation

HRID 2272970 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[O:5].[CH3:16][Mg]Br>C1COCC1.C(OCC)C>[C:11]([N:9]1[CH:10]=[C:6]([C:4](=[O:5])[CH3:16])[CH:7]=[N:8]1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 604910751-tert-butyl-1H-pyrazole-4-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, compound

Product 1

HCID 898263071460286-48-9

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, a solution of 5.87 g (27.7 mmol) 1-tert-butyl-1H-pyrazole-4-carboxylic acid methoxy-methyl-amide in 55 ml THF is cooled to 0° C. and 18.5 ml (55.5 mmol) of a 3 M solution of methylmagnesium bromide in diethyl ether is added dropwise at 0° C. The reaction mixture is stirred for 18 hours at room temperature. The reaction mixture is partitioned between brine and ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 1-(1-tert-butyl-1H-pyrazol-4-yl)-ethanone as white solid; HPLC/MS 1.87 min (B), [M+H] 167;

Workup

  1. customThe reaction mixture is partitioned between brine and ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-ca91b5263d474a198bd6ed7075376fe1
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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