Acetic Acid → Ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate

HRID 723460Notes

Reaction equation

HRID 723460 reaction equation
C([O:4][CH:5]1[CH2:10][N:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][CH:7]=[CH:6]1)(=O)C.[OH-].[Na+].C(O)(=O)C>CCO>[OH:4][CH:5]1[CH2:10][N:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][CH:7]=[CH:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 11481289HCID 11481289, compound

Product 1

HCID 13042964Ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylateYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 239B (10.5 g, 49.2 mmol) in 30 mL of EtOH was added a solution of 0.2N NaOH in EtOH (65 mL) and the mixture was stirred at 0° C. for 30 min. After warming to room temperature, the reaction mixture was neutralized with glacial acetic acid. Concentration in vacuo afforded 8.5 g of 239C as an oil. 1H-NMR (400 MHz, CDCl3): 5.90 (m, 1H), 5.82 (bs, 1H), 4.20 (bs, 1H), 4.18 (q, J=7.08, 2H), 4.04 (m, 1H), 3.85 (m, 1H), 3.55 (m, 2H), 1.28 (t, J=7.08, 3H).

Workup

  1. temperatureAfter warming to room temperature
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-ca042d465a6e4c2b97c386a4b1e6a355
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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