Hydrochloric Acid → 3,4-Dimethoxyphenyl 2-thiazolyl ketone

HRID 1068579

反応式

HRID 1068579 の反応式
C([Li])CCC.Br[C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:17]#N.Cl.C(=O)([O-])[OH:26].[Na+]>C(OCC)C.CCCCCC>[S:8]1[CH:9]=[CH:10][N:11]=[C:7]1[C:17]([C:16]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:14]([O:13][CH3:12])[CH:15]=1)=[O:26]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 748423,4-DimethoxybenzonitrileHCID 764302-BromothiazoleHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

生成物 1

HCID 211897683,4-Dimethoxyphenyl 2-thiazolyl ketone収率 46.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A hexane solution of butyllithium (9.50 mM) was dissolved in dried diethyl ether (6.5 ml) and cooled to −78° C. A solution of 2-bromothiazole (1.03 g, 6.13 mM) in diethyl ether (0.5 ml) was dropped into this solution. The solution was stirred at that temperature for 30 minutes, then a solution of 3,4-dimethoxybenzonitrile (1.00 g, 6.13 mM) in diethyl ether (3.0 ml) was added and the resultant mixture stirred for a further 6 hours. 1N Hydrochloric acid (20 ml) was poured into the solution obtained, which was then warmed to room temperature and stirred for 30 minutes, then a saturated sodium hydrogencarbonate solution was added to neutralize the solution and extraction was performed with ethyl acetate. Next, the organic layer was washed with brine and dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo to obtain a dark red solid residue. The residue was purified by flash chromatography (SiO2: eluted by gradient from 50% hexane/methylene chloride to 25% hexane/methylene chloride). The solvent was removed in vacuo and the resultant product was dried to obtain 3,4-dimethoxyphenyl 2-thiazolyl ketone 0.71 g (yield 46.5%) as a red solid.

後処理

  1. customobtained
  2. temperaturewhich was then warmed to room temperature
  3. stirringstirred for 30 minutes
  4. extractionthe solution and extraction
  5. washNext, the organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customto obtain a dark red solid residue
  9. customThe residue was purified by flash chromatography (SiO2: eluted by gradient from 50% hexane/methylene chloride to 25% hexane/methylene chloride)
  10. customThe solvent was removed in vacuo
  11. dry with materialthe resultant product was dried

出典と根拠

ORDレコード
ord-39e331ceaef847f59d5e01b8cee33013
出典データセット
uspto-grants-2001_06
特許番号
US06251897B1

関連ノート

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