Sodium Hydroxide → HCID 21882727, compound

HRID 2233521Notes

Reaction equation

HRID 2233521 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11]([O:13]C)=[O:12])[CH:4]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21882722Methyl 3-(4-methoxypyridin-2-yl)propanoate2×

Product 1

HCID 21882727HCID 21882727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

41.95 g of methyl 3-(4-methoxypyridin-2-yl)propionate (starting material C1) are dissolved in 700 ml of tetrahydrofuran, and 217 ml of 1N sodium hydroxide solution are added. The mixture is stirred at RT until no more starting material is detectable (TLC). The mixture is neutralized using 217 ml of 1N hydrochloric add solution, evaporated to dryness and dried under high vacuum. The colorless residue is ground and extracted four times with dichloromethane/methanol (9:1). The combined extracts are evaporated to dryness. This gives 33.2 g of the title compound as a colorless powder of m.p. 131-132° C. The mass spectrum shows the molecular peak MH+ at 182 Da.

Workup

  1. customevaporated to dryness
  2. customdried under high vacuum
  3. extractionextracted four times with dichloromethane/methanol (9:1)
  4. customThe combined extracts are evaporated to dryness

Sources & evidence

ORD record
ord-b43e0747fe604a469c477b2b94355bbe
Source dataset
uspto-grants-2010_05
Patent number
US07709488B2

Reaction notes

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