Triethylamine → HCID 20087667, compound

HRID 275316Notes

Reaction equation

HRID 275316 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][CH3:13])=[O:10].[OH:14][C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[O:18][C:17](=[O:25])[C:16]=1[C:26]1[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=1[CH3:34]>C(OCC)(=O)C>[CH2:12]([O:11][C:9]([O:14][C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[O:18][C:17](=[O:25])[C:16]=1[C:26]1[C:27]([CH3:34])=[CH:28][C:29]([CH3:33])=[CH:30][C:31]=1[CH3:32])=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 56635483HCID 56635483, compound

Product 1

HCID 20087667HCID 20087667, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

2.0 g (20 mmol) of triethylamine and subsequently 2.2 g (20 mmol) of ethyl chloroformate in 20 ml of ethyl acetate are added dropwise at 0° C. to 5.7 g (20 mmol) of 4-hydroxy-6-tert.-butyl-3-(2,4,6-trimethylphenyl)pyrone in 50 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 (20:1 parts by volume). 6.0 g of 4-ethoxycarbonyloxy-6-tert.-butyl-3-(2,4,6-trimethylphenyl)pyrone are obtained (yield: 84% of theory). M.p.=92°-94° 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-417cc9d1b50a4e49948cbf022ffc3ab4
Source dataset
uspto-grants-1995_02
Patent number
US05393729

Reaction notes

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