Triethylamine → HCID 15107320, compound

HRID 274206Notes

Reaction equation

HRID 274206 reaction equation
C(N(CC)CC)C.[CH:8]([C:11]1[CH:15]=[C:14]([CH:16]2[O:21][C:20](=[O:22])[CH2:19][C:18](=[O:23])[CH2:17]2)[O:13][N:12]=1)([CH3:10])[CH3:9].[C:24](Cl)(=[O:28])[CH2:25][CH2:26][CH3:27]>C1COCC1>[C:24]([CH:19]1[C:18](=[O:23])[CH2:17][CH:16]([C:14]2[O:13][N:12]=[C:11]([CH:8]([CH3:10])[CH3:9])[CH:15]=2)[O:21][C:20]1=[O:22])(=[O:28])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 15107319HCID 15107319, compound

Product 1

HCID 15107320HCID 15107320, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

12.6 g of triethylamine was added to 27.9 g of 6-(3-isopropylisoxazol-5-yl)-tetrahydropyran-2,4-dione in 200 ml of THF. At 0° C., 13.3 g of butyryl chloride was dripped in and the mixture was stirred for one hour at 0° C. The mixture was evaporated, followed by partitioning between methylene chloride and water. The organic phase was worked up, i.e., extracted with water, 10% strength sodium carbonate solution and again with water, dried with sodium sulfate and evaporated again. The residue was dissolved in anhydrous methylene chloride and stirred for 48 hours with 1.3 g of 4-(N,N-dimethylamino)-pyridine. Removal of the solvent was followed by chromatography over silica gel with methylene chloride and methanol (98.5:1.5). The isolated compound was recrystallized from a small amount of cyclohexane. There was obtained 13 g of product.

Workup

  1. customAt 0° C.
  2. customThe mixture was evaporated
  3. customby partitioning between methylene chloride and water
  4. extractioni.e., extracted with water, 10% strength sodium carbonate solution and again with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated again
  7. dissolutionThe residue was dissolved in anhydrous methylene chloride
  8. stirringstirred for 48 hours with 1.3 g of 4-(N,N-dimethylamino)-pyridine
  9. customRemoval of the solvent
  10. customThe isolated compound was recrystallized from a small amount of cyclohexane

Sources & evidence

ORD record
ord-e42882b0d17a49878d31e8a95fd34d0f
Source dataset
uspto-grants-1995_02
Patent number
US05389602

Reaction notes

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