Triethylamine → HCID 15729829, compound

HRID 1905338Notes

Reaction equation

HRID 1905338 reaction equation
C(N(CC)CC)C.[S:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]2[CH2:19][O:18][C:17](=[O:20])[CH2:16][C:15]2=[O:21])[CH2:9]1.[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>O1CCCC1.O>[C:22]([CH:16]1[C:15](=[O:21])[CH:14]([CH:10]2[CH2:11][CH2:12][CH2:13][S:8][CH2:9]2)[CH2:19][O:18][C:17]1=[O:20])(=[O:25])[CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 15729828HCID 15729828, compound

Product 1

HCID 15729829HCID 15729829, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.4 g of triethylamine is added to 5 g of 5-(tetrahydrothiopyran-3-yl)-tetrahydropyran-2,4-dione in 50 ml of anhydrous tetrahydrofuran. At 0° C., 2.2 g of propionyl chloride is dripped in and the mixture is stirred for 12 hours at room temperature. The mixture is then diluted with 150 ml of water, and the aqueous phase is separated and extracted with 100 ml of ether. The combined organic phases are washed once with ice-cold 5% strength hydrochloric acid and once with water, and dried with magnesium sulfate, and the solvent is removed. The oily residue is dissolved in 50 ml of anhydrous toluene, 0.3 g of 3-dimethylaminopyridine is added, and the mixture is stirred at 80° C. for 2 hours. After cooling, extraction is carried out twice with 25 ml of hydrochloric acid and twice with 25 ml of water. The organic phase is dried over sodium sulfate and concentrated in a rotary evaportor. The residue is chromatographed with methylene chloride on silica gel. There is obtained 1.8 g of the desired compound.

Workup

  1. customAt 0° C.
  2. customthe aqueous phase is separated
  3. extractionextracted with 100 ml of ether
  4. washThe combined organic phases are washed once with ice-cold 5% strength hydrochloric acid and once with water
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent is removed
  7. dissolutionThe oily residue is dissolved in 50 ml of anhydrous toluene
  8. addition0.3 g of 3-dimethylaminopyridine is added
  9. stirringthe mixture is stirred at 80° C. for 2 hours
  10. temperatureAfter cooling
  11. extractionextraction
  12. dry with materialThe organic phase is dried over sodium sulfate
  13. concentrationconcentrated in a rotary evaportor
  14. customThe residue is chromatographed with methylene chloride on silica gel

Sources & evidence

ORD record
ord-5c9fce7f7b1d432e9a23e400e4af2ce1
Source dataset
uspto-grants-1989_06
Patent number
US04842638

Reaction notes

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