Boron Trichloride → ethyl 1-methyl-1H-pyrazole-4-carboxylate

HRID 2397643Notes

Reaction equation

HRID 2397643 reaction equation
ClC1C=CC([C:8]2[N:9]([CH3:18])[N:10]=[CH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=C(C(OC)C2C=CC=CC=2F)C=1.B(Cl)(Cl)Cl>C(Cl)Cl>[CH2:16]([O:15][C:13]([C:12]1[CH:11]=[N:10][N:9]([CH3:18])[CH:8]=1)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 20321570HCID 20321570, compound

Product 1

HCID 11116265ethyl 1-methyl-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 20.1 g of 3-[4-chloro-2-(2-fluoro-α-methoxy-benzyl)-phenyl]-4-ethoxycarbonyl-2-methyl-pyrazole in 250 ml methylene chloride is added 54 ml of a 1.4 molar boron trichloride solution in methylene chloride, and the mixture is stirred during 16 hours. Ice/water is then added; the organic layer separated, washed with a saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The aqueous layers are reextracted with methylene chloride. After removal of the solvent, the 3-[4-chloro-2-fluoro-benzyl)-phenyl]-4-ethoxycarbonyl-2-methyl-pyrazole is obtained as the solid residue, which is directly used in the next step.

Workup

  1. customthe organic layer separated
  2. washwashed with a saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of the solvent

Sources & evidence

ORD record
ord-d7387b6d8cff4b7b9c0f45872cc15231
Source dataset
uspto-grants-1977_05
Patent number
US04022800

Reaction notes

Loading…