Chloromethyl Methyl Ether → Ethyl 3-tert-butyl-1-(methoxymethyl)-1H-pyrazole-5-carboxylate

HRID 217879Notes

Reaction equation

HRID 217879 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:22][O:23][CH3:24].CCOC(C)=O>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH2:22][O:23][CH3:24])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2743509Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate

Product 1

HCID 59588852Ethyl 3-tert-butyl-1-(methoxymethyl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Method I was used with ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate (1078 mg, 5.49 mmol), caesium carbonate (2.89 g, 8.87 mmol) and chloro(methoxy)methane (426 μl, 5.60 mmol). 16 hours reaction time. Column eluent: 0→10% EtOAc in CH2Cl2. Yield: 485 mg (37%) of a colorless oil.

Workup

  1. custom16 hours reaction time

Sources & evidence

ORD record
ord-0b818e8ce98a4eebbd6cd2f6eb9b560a
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

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