Methanol → HCID 67319803, compound

HRID 2194847Notes

Reaction equation

HRID 2194847 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:20]=[C:21]1[N:25]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[N:24]=[C:23]([C:36]([O:38][CH3:39])=[O:37])[CH2:22]1.CO.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O.C1C=CC=CC=1>[CH3:1][O:20][C:21]1[N:25]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=2)[N:24]=[C:23]([C:36]([O:38][CH3:39])=[O:37])[CH:22]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44542635HCID 44542635, compound

Product 1

HCID 67319803HCID 67319803, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL round-bottomed flask was charged with triphenylphosphine (6.9 g, 26 mmol), methyl 5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylate 71 (5.0 g, 17 mmol), MeOH (0.88 mL, 22 mmol), and 200 mL of benzene. After cooling to 0° C., diisopropyl azodicarboxylate (DIAD) (5.2 mL, 26 mmol) was added dropwise. The mixture was stirred at room temperature for 18 h, then diluted with water and extracted with CH2Cl2. The combined extracts were dried and concentrated to give an oil that was purified by column chromatography on silica gel (5% to 40% EtOAc in hexanes) to give methyl 5-methoxy-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate 72.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe combined extracts were dried
  3. concentrationconcentrated
  4. customto give an oil that
  5. customwas purified by column chromatography on silica gel (5% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b83c82415a724710a49f345e7791678c
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

Loading…