Morpholine → 4-Hydroxy-4,5-dimethyl-2-trimethylsilanyl-dihydrothiophene-3-carboxylic acid allylamide

HRID 370313

反応式

HRID 370313 の反応式
[SH:1][CH:2]([CH3:6])[C:3](=[O:5])[CH3:4].N1CCOCC1.[CH2:13]([NH:16][C:17](=[O:24])[C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[CH2:15]>C(OCOCC)C>[CH2:13]([NH:16][C:17]([CH:18]1[C:3]([OH:5])([CH3:4])[CH:2]([CH3:6])[S:1][CH:19]1[Si:20]([CH3:21])([CH3:22])[CH3:23])=[O:24])[CH:14]=[CH2:15]

参加物

5

反応物 3

HCID 8083MorpholineHCID 386793-Mercapto-2-butanone3 回HCID 11217610N-allyl-3-trimethylsilylpropiolic amide

生成物 1

HCID 701454464-Hydroxy-4,5-dimethyl-2-trimethylsilanyl-dihydrothiophene-3-carboxylic acid allylamide収率 84%

試薬・触媒・溶媒 1

HCID 10024Diethoxymethane溶媒

実験手順

A solution of 3-mercapto-2-butanone (2.1 g, 0.020 mol) and morpholine (1.5 g, 0.017 mol) in diethoxymethane (20 mL) was heated to reflux and treated with N-allyl-3-trimethylsilylpropiolic amide (3.04 g, 0.017 mol). The mixture is heated at reflux under a nitrogen atmosphere overnight. An additional portion of the 3-mercapto-2-butanone (0.7 g, 0.0067 mol) was added, and heating was continued for 4 hours more. A final portion of the 3-mercapto-2-butanone (0.7 g, 0.0067 mol) was added, heating was continued for 4 hours at reflux, then the mixture was cooled and evaporated under reduced pressure. The residue was extracted with two 40 mL portions of hot heptane, filtered, and allowed to cool (ice/salt bath). The resulting solid precipitate was collected by filtration and dried to give 4.0 g of 4-hydroxy-4,5-dimethyl-2-trimethylsilanyl-dihydrothiophene-3-carboxylic acid allylamide (84% yield).

後処理

  1. temperatureto reflux
  2. temperatureThe mixture is heated
  3. temperatureat reflux under a nitrogen atmosphere overnight
  4. temperatureheating
  5. temperatureheating
  6. waitwas continued for 4 hours
  7. temperatureat reflux
  8. temperaturethe mixture was cooled
  9. customevaporated under reduced pressure
  10. extractionThe residue was extracted with two 40 mL portions of hot heptane
  11. filtrationfiltered
  12. temperatureto cool (ice/salt bath)
  13. filtrationThe resulting solid precipitate was collected by filtration
  14. customdried

出典と根拠

ORDレコード
ord-da4fd3de976e4fca9523abb5cfbba84b
出典データセット
uspto-grants-2000_10
特許番号
US06140511

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