Acetic Acid → HCID 178469765, compound

HRID 1894317Notes

Reaction equation

HRID 1894317 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])O[CH:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[NH4+:21].C(O)(=O)C>C(O)C.O>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[C:11]([OH:12])=[CH:10][C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:21][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 15073226Ethyl 6-tert-butyl-4-oxo-4H-pyran-3-carboxylate

Product 1

HCID 178469765HCID 178469765, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
95 °C

Procedure

6-tert-Butyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester (300 mg, 1.34 mmol, prepared according to the literature procedure by McCombie, S. W. et al. J. Org. Chem. 1991, 56, 4963-4967) and ammonium acetate (300 mg, 4.16 mmol) were combined in ethanol/water (8 mL/3 ml). Acetic acid was added and reaction mixture was heated at 95° C. for 30 min. It was concentrated and basified with aqueous sodium hydroxide and extracted with methylene chloride (2×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 6-tert-butyl-4-hydroxy-nicotinic acid ethyl ester as a white solid (230 mg, 76%). LR-MS: 224 [(M+H)+]

Workup

  1. customreaction mixture
  2. concentrationIt was concentrated
  3. extractionextracted with methylene chloride (2×20 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9a0c4c3d40ec40568a8f3632aa9ffeab
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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