Ethyl 3-oxovalerate → ethyl 6,7-dihydro-4-ethyl-2-phenyl-4H-pyrano[4,3-d]thiazole-4-acetate

HRID 258578Notes

Reaction equation

HRID 258578 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=O)[CH2:16][CH3:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:16]([C:15]1([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:9]2[S:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:11][C:10]=2[CH2:12][CH2:13][O:14]1)[CH3:17]

Participants

5

Reactant 3

HCID 78656Ethyl 3-oxovalerateHCID 521998p-Toluenesulfonic acid monohydrateHCID 106083152-Phenyl-4-(beta-hydroxyethyl)thiazole

Product 1

HCID 53824828ethyl 6,7-dihydro-4-ethyl-2-phenyl-4H-pyrano[4,3-d]thiazole-4-acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the starting material of formula II, 2-phenyl-4-(β-hydroxyethyl)thiazole (30.8 g, 0.15 mole, described in Example 1), ethyl propionylacetate (28.8 g, 0.2 mole) and p-toluene-sulfonic acid hydrate (0.25 mole) in toluene (1200 ml) is heated at reflux temperature, with water separation, for 17 hr. Additional ethyl propionylacetate (6 g) and p-toluenesulfonic acid hydrate is added and refluxing is continued for 24 hr. The mixture is evaporated under reduced pressure and the residue is triturated with petroleum ether. The residue is dissolved in a mixture of aqueous sodium bicarbonate solution and ether. The organic solution is separated, dried over sodium sulfate and evaporated under reduced pressure to give ethyl 6,7-dihydro-4-ethyl-2-phenyl-4H-pyrano[4,3-d]thiazole-4- acetate (IV, R1 = H, R2 = CH2CH3, A= COOCH2CH3 and n= 1).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature
  3. customwith water separation
  4. additionAdditional ethyl propionylacetate (6 g) and p-toluenesulfonic acid hydrate is added
  5. temperaturerefluxing
  6. waitis continued for 24 hr
  7. customThe mixture is evaporated under reduced pressure
  8. customthe residue is triturated with petroleum ether
  9. dissolutionThe residue is dissolved in a mixture of aqueous sodium bicarbonate solution and ether
  10. customThe organic solution is separated
  11. dry with materialdried over sodium sulfate
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3703f265c11444b38a1a1c341a199578
Source dataset
uspto-grants-1977_07
Patent number
US04033977

Reaction notes

Loading…