Trifluoroacetic acid → HCID 178469925, compound

HRID 2064669Notes

Reaction equation

HRID 2064669 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:11][O:12]C(C)(C)C)=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:11][OH:12])=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178469926HCID 178469926, compound

Product 1

HCID 178469925HCID 178469925, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-tert-butyloxymethyl-1H-pyrazole-4-carboxylic acid ethyl ester [3.46 g, Reference Example 42] in dichloromethane (25 ml) was treated with trifluoroacetic acid (25 ml). The mixture was stirred for 1.5 hours and then concentrated. The residue was partitioned between saturated sodium carbonate solution and ethyl acetate. The organic layer was dried over magnesium sulfate and then evaporated to give 3-hydroxymethyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.49 g) as a brown solid which was used without further purification. LC-MS (METHOD B): RT=2.54 minutes; 171 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between saturated sodium carbonate solution and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-3a8701767a294dd5a2d14da99d53c275
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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