Pyrazole → 1-Benzyloxymethyl-1H-pyrazole

HRID 1959557Notes

Reaction equation

HRID 1959557 reaction equation
Cl[CH2:2][O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH:11]1[CH:15]=[CH:14][CH:13]=[N:12]1>CN(C=O)C>[CH2:4]([O:3][CH2:2][N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 1048PyrazoleHCID 137983Benzyl chloromethyl ether

Product 1

HCID 216869571-Benzyloxymethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloromethoxymethyl-benzene (purity ˜60%, 2.0 mL, 14 mmol) was added dropwise to a stirred solution of 1H-pyrazole (1.93 g, 28.4 mmol) in DMF (10 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for an additional 1.5 h. The reaction was then quenched by the addition of concentrated aqueous NH3 (1 mL). The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 1:20) to give the title compound. MS (m/z): 189.0 [M+H+].

Workup

  1. customThe reaction was then quenched by the addition of concentrated aqueous NH3 (1 mL)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 1:20)

Sources & evidence

ORD record
ord-9d308450e0ba4cfea95a78f1dfa75c7f
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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