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

HRID 1267778ノート

反応式

HRID 1267778 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
10 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5df879eace7e4b829809aad12e653c20
出典データセット
uspto-grants-2003_04
特許番号
US06552068B1

反応ノート

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