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

HRID 1596701

반응식

HRID 1596701 반응식
[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]

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 386793-Mercapto-2-butanone3회HCID 11217610N-allyl-3-trimethylsilylpropiolic amide

생성물 1

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

시약·촉매·용매 1

HCID 10024Diethoxymethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ce6ca6612395442b8182abe8a980d289
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291513B1

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