Methanol → HCID 117724778, compound

HRID 628539Notes

Reaction equation

HRID 628539 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH3:18])[CH:9]=2)[C:3]=1[CH:19]=[O:20].[O:21]1CCC[CH2:22]1.CO.[H-].[Na+]>O>[CH:19]([C:3]1[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH3:18])[CH:9]=2)=[N:5][N:6]([CH3:7])[C:2]=1[O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 118001333HCID 118001333, compound

Product 1

HCID 117724778HCID 117724778, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, to a mixture of 5-chloro-4-formyl-3-(4-isopropoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole (described in Reference Preparation example 96) 4.8 g and tetrahydrofuran 100 ml was added methanol 0.6 g and 55% sodium hydride 0.8 g, and the resulting mixture was stirred for three hours. To the reaction mixture was added water 50 ml, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 4-formyl-3-(4-isopropoxy-3-methyl-phenyl)-5-methoxy-1-methyl-1H-pyrazole 4.5 g.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-185b5d8324e1470182dac15df6441e19
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…