Dimethylformamide dimethyl acetal → Methyl alpha-[(Z)-methoxy methylene]-4-[(E)-styryl]-5-thiazolacetate

HRID 37612Notes

Reaction equation

HRID 37612 reaction equation
[CH:1](/[C:9]1[N:10]=[CH:11][S:12][C:13]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:19][O:20][CH:21](OC)N(C)C>>[CH3:19][O:20]/[CH:21]=[C:14](\[C:13]1[S:12][CH:11]=[N:10][C:9]=1[CH:1]=[CH:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)/[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67766698HCID 67766698, compound

Product 1

HCID 67739509Methyl alpha-[(Z)-methoxy methylene]-4-[(E)-styryl]-5-thiazolacetate

Conditions

Temperature
50 °C

Procedure

A mixture of 2.5 g of the product of Step A and 25 ml of dimethylformamide dimethyl acetal was heated to 50° C. and after 4 hours at this temperature, the mixture was allowed to return to 25° C. The reaction mixture was evaporated to dryness and the residue was dissolved in 30 ml of tetrahydrofuran and 5 ml of an aqueous solution of 2N hydrochloric acid. After standing for 2 hours at 25° C., the mixture was decanted followed by extraction with methylene chloride. The organic phase was dried over magnesium sulfate, filtered and evaporated to dryness. The residue was dissolved in 30 ml of acetone and 4 g of potassium carbonate and 6 ml of methyl iodide were added. The mixture was stirred for 16 hours at 20° to 25° C. and after filtering and evaporating to dryness, the residue was chromatographed on silica, eluting with a hexane--ethyl acetate mixture (7-3) to obtain 1.1 g of the desired product. Thin layer chromatography; Rf=0.17 [eluant: hexane--acetate of ethyl (7-3)].

Workup

  1. customto return to 25° C
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in 30 ml of tetrahydrofuran
  4. customthe mixture was decanted
  5. extractionfollowed by extraction with methylene chloride
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. dissolutionThe residue was dissolved in 30 ml of acetone
  10. addition4 g of potassium carbonate and 6 ml of methyl iodide were added
  11. filtrationafter filtering
  12. customevaporating to dryness
  13. customthe residue was chromatographed on silica
  14. washeluting with a hexane

Sources & evidence

ORD record
ord-ff230fb56db045889852486b78027e73
Source dataset
uspto-grants-1995_05
Patent number
US05420340

Reaction notes

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