Sodium Hydroxide → HCID 58105226, compound

HRID 1172235Notes

Reaction equation

HRID 1172235 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58105215HCID 58105215, compound

Product 1

HCID 58105226HCID 58105226, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-[6-(t-butyldimethylsilanyloxymethyl)pyridin-2-yl]propionate (5.07 g) was dissolved in 100 mL of ethanol, and 23.5 mL of 1N aqueous sodium hydroxide was added to the solution, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated to approximate half volume thereof under reduced pressure, after adding ice-water, the solution was acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (chloroform-methanol=10:1) to give 2.77 g of 3-[6-(t-butyldimethylsilanyloxymethyl)pyridin-2-yl]propionic acid as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated to approximate half volume
  2. additionunder reduced pressure, after adding ice-water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-a46d9372866140bcbbfd5f954c35a217
Source dataset
uspto-grants-2010_11
Patent number
US07834002B2

Reaction notes

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