Triethylamine → HCID 11058212, compound

HRID 1369294Notes

Reaction equation

HRID 1369294 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[O:5][C:4](=[O:15])[C:3]=1[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24].C(N(CC)CC)C.[CH2:32]([O:35][CH2:36]Cl)[C:33]#[CH:34]>C(OCC)(=O)C>[CH3:8][C:7]1[C:2]([O:1][CH2:36][O:35][CH2:32][C:33]#[CH:34])=[C:3]([C:16]2[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=2[CH3:22])[C:4](=[O:15])[O:5][C:6]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122413411-Propyne, 3-(chloromethoxy)-HCID 54696216HCID 54696216, compound

Product 1

HCID 11058212HCID 11058212, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

6.4 g (20 mmol) of 4-hydroxy-5-methyl-6-(2-pyridyl)-3-(2,4,6-trimethylphenyl)-2-pyrone in 50 ml of ethyl acetate are introduced in the absence of moisture. 2.02 g (20 mmol) of triethylamine are added thereto at 20° C. and a solution of 2.1 g (20 mmol) of propargyloxychloromethane in 20 ml of ethyl acetate is added dropwise at 0° C. with cooling. The mixture is further stirred for 20 h at 20° C. and the reaction is followed by thin-layer chromatography. The solution is filtered off from the precipitated triethylamine hydrochloride with suction and washed with ethyl acetate. The combined mother liquors are washed twice, each time with 50 ml of half-saturated common salt solution, dried over magnesium sulfate and evaporated in vacuo. 8 g of crude product are obtained. 6.4 g (82% of theory) of 5-methyl-6-(2-pyridyl)-4-propargyloxymethoxy-3-(2,4,6-trimethylphenyl)-2-pyrone are obtained as an oil by flash chromatography on 500 g of silica gel 60 (35-70 μm) using toluene:acetone 20:1 as mobile phase.

Workup

  1. temperaturewith cooling
  2. filtrationThe solution is filtered off from the precipitated triethylamine hydrochloride with suction
  3. washwashed with ethyl acetate
  4. washThe combined mother liquors are washed twice
  5. dry with materialeach time with 50 ml of half-saturated common salt solution, dried over magnesium sulfate
  6. customevaporated in vacuo
  7. custom8 g of crude product are obtained

Sources & evidence

ORD record
ord-8252fa52d60245eead628b280ffd419a
Source dataset
uspto-grants-2003_06
Patent number
US06576771B1

Reaction notes

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