8-(t-Butyldimethylsilyloxy)-1-octyne → 4-[8-(t-Butyldimethylsilyloxy)-1-octynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792348노트

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HRID 1792348 반응식
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](=[O:43])[C:29]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)([CH3:34])[CH2:30][S:31]2)=[CH:26][CH:25]=1>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:28]1([OH:43])[C:27]2[C:32](=[CH:33][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[S:31][CH2:30][C:29]1([C:35]1[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1)[CH3:34])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 104217908-(t-Butyldimethylsilyloxy)-1-octyneHCID 109799547-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-oneHCID 178418339Butyllithium

생성물 1

HCID 220330184-[8-(t-Butyldimethylsilyloxy)-1-octynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman수율 870.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

8-(t-Butyldimethylsilyloxy)-1-octyne (12 g, 49.9 mmol) was dissolved in dry tetrahydrofuran (150 ml) under argon atmosphere and then cooled to −78C. 2.5M n-Butyllithium (18 ml, 44.9 mmol) was added dropwise thereto, and the mixture was warmed to −10° C. and stirred for 1 hour and then cooled to −78° C. 7-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (860 mg,2.9 mmol) was added portionwise and then warmed to room temperature and stirred for 1.5 hour. The mixture was quenched by water. The reaction solvent was evaporated off, then the residue was dissolved in ethyl acetate, which was washed with water. The organic solvent was dried over anhydrous magnesium sulfate and removed by evaporation under vacuum. This product was purified by column chromatography on silica gel, eluting with 10% ethyl acetate in n-hexane. After removal of the solvent, 14 g of the title compound was obtained as colorless oil. (yield: 99.3%)

후처리

  1. temperaturecooled to −78C
  2. temperaturecooled to −78° C
  3. temperaturewarmed to room temperature
  4. stirringstirred for 1.5 hour
  5. customThe mixture was quenched by water
  6. customThe reaction solvent was evaporated off
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwhich was washed with water
  9. dry with materialThe organic solvent was dried over anhydrous magnesium sulfate
  10. customremoved by evaporation under vacuum
  11. customThis product was purified by column chromatography on silica gel
  12. washeluting with 10% ethyl acetate in n-hexane
  13. customAfter removal of the solvent

출처 및 근거

ORD 기록
ord-0687bd6360714687a6b4063ebd39624c
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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