Water → 7-Methoxy-3-(4-methoxyphenyl)-3-(2-propenyl)thiochroman-4-one

HRID 1267778노트

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HRID 1267778 반응식
[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:25])[CH:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:13][S:14]2)=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].O>CS(C)=O>[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:25])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)([CH2:3][CH:2]=[CH2:1])[CH2:13][S:14]2)=[CH:9][CH:8]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7841Allyl bromideHCID 111303687-Methoxy-3-(4-methoxyphenyl)thiochroman-4-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 185462817-Methoxy-3-(4-methoxyphenyl)-3-(2-propenyl)thiochroman-4-one수율 79%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

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온도
10 °C

실험 절차

Allyl bromide (5.7 ml, 66.56 mmol) was added dropwise to a solution of 7-methoxy-3-(4-methoxyphenyl)thiochroman-4-one (2 g, 6.64 mmol) in dimethyl sulfoxide (34 ml). To this mixture, a solution of potassium tert-butoxide (5.22 g, 46.55 mmol) in dimethyl sulfoxide (70 ml) was slowly added dropwise at 10° C., followed by stirring for 2 hours at 10° C. and for 15 hours at room temperature. Water was added to the reaction mixture, which was then extracted three times with ethyl acetate. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent:ethyl acetate/hexane=1/9) to give 7-methoxy-3-(4-methoxyphenyl)-3-(2-propenyl)thiochroman-4-one (1.78 g, Yield 79%) as a colorless oil.

후처리

  1. extractionwas then extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate/hexane=1/9)

출처 및 근거

ORD 기록
ord-5df879eace7e4b829809aad12e653c20
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552068B1

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