Dimethylformamide → 2-Benzyloxymethyl-2H-pyrazole-3-carbaldehyde

HRID 660490Notes

Reaction equation

HRID 660490 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN([CH:23]=[O:24])C>C1COCC1>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([CH:23]=[O:24])=[CH:13][CH:12]=[N:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 216869571-Benzyloxymethyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 866325702-Benzyloxymethyl-2H-pyrazole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1-benzyloxymethyl-1H-pyrazole (4.6 g, 24 mmol) in THF (40 mL) is cooled to −78° C. n-Butyllithium (12 mL, 2.5 M in hexanes, 30 mmol) is added dropwise. After stirring at −78° C. for 30 min, DMF (1.0 mL) is added. The reaction mixture is warmed to RT over 1 h. The mixture is partitioned between aqueous NH4Cl and EtOAc. The organic layer is concentrated to afford the title compound as a yellow oil, which is used directly in the next step: (M+1)+=217.

Workup

  1. additionis added dropwise
  2. temperatureThe reaction mixture is warmed to RT over 1 h
  3. customThe mixture is partitioned between aqueous NH4Cl and EtOAc
  4. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-1d07c674f5aa4fefb268365ceab98bb6
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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