Acetyl chloride → HCID 20087668, compound

HRID 275315Notes

Reaction equation

HRID 275315 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[CH2:12]([O:14][C:15]([C:17]1[C:18]([OH:34])=[C:19]([C:25]2[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=2[CH3:33])[C:20](=[O:24])[O:21][C:22]=1[CH3:23])=[O:16])[CH3:13]>C(OCC)(=O)C>[C:8]([O:34][C:18]1[C:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])=[C:22]([CH3:23])[O:21][C:20](=[O:24])[C:19]=1[C:25]1[C:26]([CH3:33])=[CH:27][C:28]([CH3:32])=[CH:29][C:30]=1[CH3:31])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54725947HCID 54725947, compound

Product 1

HCID 20087668HCID 20087668, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

1.0 g (10 mmol) of triethylamine and then 0.8 g (10 mmol) of acetyl chloride are added dropwise at 0° C. to 3.2 g (10 mmol) of 5-ethoxycarbonyl-4-hydroxy-6-methyl-3-(2,4,6-trimethylphenyl)pyrone in ml of ethyl acetate. The mixture is stirred for 20 hours at 20° C. and filtered, the organic phase is washed with semi-concentrated sodium chloride solution and dried over sodium sulphate and the solvent is evaporated in vacuo. The residue is chromatographed on silica gel (35-70 μm) using toluene/acetone (40:1 parts by volume). 2.9 g of 4-acetoxy-5-ethoxycarbonyl-6-methyl-3-(2,4,6-trimethylphenyl)pyrone are obtained (yield: 81% of theory). M.p.=107° to 109° C.

Workup

  1. filtrationfiltered
  2. washthe organic phase is washed with semi-concentrated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is evaporated in vacuo
  5. customThe residue is chromatographed on silica gel (35-70 μm)

Sources & evidence

ORD record
ord-b6877121e86840e4907d514f9bf08745
Source dataset
uspto-grants-1995_02
Patent number
US05393729

Reaction notes

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