Trimethylamine → 6-Methyl-4-oxo-4H-pyran-3-yl benzoate

HRID 1928673Notes

Reaction equation

HRID 1928673 reaction equation
[CH3:1][C:2]1[O:8][CH:7]=[C:6]([OH:9])[C:4](=[O:5])[CH:3]=1.CN(C)C.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:14]([O:9][C:6]1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[O:8][CH:7]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 7412Benzoyl chlorideHCID 695214H-Pyran-4-one, 5-hydroxy-2-methyl-

Product 1

HCID 442012016-Methyl-4-oxo-4H-pyran-3-yl benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Allomaltol (600 mg; 4.76 mmol) was weighed out into a round bottom flask (100 ml) containing a stir-bar. The contents were diluted with anhydrous THF (˜20 ml) and stirred (˜5 min) to afford a solution. Next, trimethyl amine (833 μl; 6.33 mmol; 1.33 equiv.) was added drop-wise and the contents stirred (˜5 min). Benzoyl chloride (517 μl; 627 mg; 4.46 mmol) was then added drop-wise, capped and stirred at room temperature. The reaction was monitored via silica gel TLC. Once complete, the reaction mixture was concentrated under reduced pressure and the contents purified by silica gel chromatography to afford 930 mg of light yellow crystalline product (4.04 mmol; 91% yield). This compound was found to have an EC50 of >1 mM. 1H NMR (DMSO-d6) δ 8.58 (s, 1H; 2-H); 8.09-8.07 (dd, 2H); 7.78-7.76 (t, 1H); 7.63-7.59 (t, 2H); 6.43 (s, 1H; 5-H); 2.34 (s, −3H; 6-CH3).

Workup

  1. addition(100 ml) containing a stir-bar
  2. customto afford a solution
  3. stirringthe contents stirred (˜5 min)
  4. customcapped
  5. stirringstirred at room temperature
  6. concentrationOnce complete, the reaction mixture was concentrated under reduced pressure
  7. customthe contents purified by silica gel chromatography

Sources & evidence

ORD record
ord-1513b34a5606429abddff621247b8600
Source dataset
uspto-grants-2012_05
Patent number
US08183398B2

Reaction notes

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