Sodium Bicarbonate → HCID 68295278, compound

HRID 1850074Notes

Reaction equation

HRID 1850074 reaction equation
[Na].C([O-])(O)=O.[Na+].C([N:10]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])[CH:12]=[N:11]1)(=O)C>CO>[NH:10]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])[CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 25137630Methyl (2E)-3-(1-acetyl-1H-pyrazol-4-yl)prop-2-enoate

Product 1

HCID 68295278HCID 68295278, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydrogenocarbonate, NaHCO3 (32 g, 1.15 equiv), was added to a suspension of protected compound, (E)-methyl 3-(1-acetyl-1H-pyrazol-4-yl)acrylate (65 g, 0.33 mol), in MeOH (600 mL). The mixture was stirred for 7 h at room temperature. The solids were then filtered and washed with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (Hexane/EtOAc 8:1 to 1:2) to give the title compound as a solid (47 g, 92%).

Workup

  1. filtrationThe solids were then filtered
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (Hexane/EtOAc 8:1 to 1:2)

Sources & evidence

ORD record
ord-5aff4ddb8ad8467c9eb1aac4adf750e5
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

Loading…