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

HRID 1464412ノート

反応式

HRID 1464412 の反応式
[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]

参加物

3

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67766698HCID 67766698、化合物

生成物 1

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

反応条件

温度
50 °C

実験手順

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)].

後処理

  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-ethyl acetate mixture (7-3)

出典と根拠

ORDレコード
ord-2b54a333f53e43729eca2552a4450c00
出典データセット
uspto-grants-1994_04
特許番号
US05304653

反応ノート

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