trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene → 1-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3']bipyridinyl-4-one

HRID 1691832노트

반응식

HRID 1691832 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[N:8][S:9]([CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])(=[O:11])=[O:10])[CH:2]=1.CO/[CH:20]=[CH:21]/[C:22]([O:24][Si](C)(C)C)=[CH2:23]>C1(C)C=CC=CC=1>[CH3:15][Si:14]([CH3:17])([CH3:16])[CH2:13][CH2:12][S:9]([N:8]1[CH:20]=[CH:21][C:22](=[O:24])[CH2:23][CH:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)(=[O:11])=[O:10]

참가 물질

4

반응물 2

HCID 5366448trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadieneHCID 669074992-Trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamide

생성물 1

HCID 593777611-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3']bipyridinyl-4-one수율 40%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 2-trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamide (665 mg) in toluene (4.5 mL) was added Danishefsky's diene (0.46 mL, 2.4 mmol) under Ar atmosphere. The mixture was heated at reflux for 90 minutes. The toluene was removed in vacuo and the residue was dissolved in dichloromethane (ca. 10 mL) and treated with 2N HCl (ca. 10 mL) for 5 minutes. 10% Aqueous sodium bicarbonate was added carefully to adjust to pH 8. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and evaporated to dryness under reduced pressure. Purification of the residue by flash chromatography (gradient hexane/ethyl acetate) gave 1-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (322 mg, 40% overall).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. customThe toluene was removed in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane (ca. 10 mL)
  5. additiontreated with 2N HCl (ca. 10 mL) for 5 minutes
  6. addition10% Aqueous sodium bicarbonate was added carefully
  7. customThe phases were separated
  8. extractionthe aqueous phase was extracted with dichloromethane
  9. dry with materialThe combined organic extracts were dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated to dryness under reduced pressure
  12. customPurification of the residue by flash chromatography (gradient hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-38e7220ae01b4dd0a0d01cb1ec3efad7
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153809B2

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