Carbon Dioxide → 3-(4-methylphenyl)-2H-1-benzopyran-6-carboxylic acid

HRID 1169352ノート

反応式

HRID 1169352 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[CH:7][C:6]=2[CH:18]=1.C([Li])CCC.[C:24](=[O:26])=[O:25].Cl>C1COCC1.CCCCCC>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH2:9][O:10][C:5]3[CH:4]=[CH:3][C:2]([C:24]([OH:26])=[O:25])=[CH:18][C:6]=3[CH:7]=2)=[CH:12][CH:13]=1

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 229901326-bromo-3-(4-methylphenyl)-2H-1-benzopyranHCID 178418339Butyllithium

生成物 1

HCID 229901283-(4-methylphenyl)-2H-1-benzopyran-6-carboxylic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Into a solution of 6-bromo-3-(4-methylphenyl)-2H-1-benzopyran (0.5 g) in THF (15 ml) was added at −78° C. 1.6 M butyl lithium (a hexane solution) (1.14 ml) under a nitrogen atmosphere. The resulting mixture was stirred at −78° C. for one hour, was then mixed with dry ice and was stirred for additional one hour. After addition of 1 N hydrochloric acid (10 ml), the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the resulting crystals were collected by filtration, and the crystals were washed with diethyl ether and hexane to obtain 3-(4-methylphenyl)-2H-1-benzopyran-6-carboxylic acid (218 mg) as colorless crystals.

後処理

  1. stirringwas stirred for additional one hour
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. filtrationthe resulting crystals were collected by filtration
  7. washthe crystals were washed with diethyl ether and hexane

出典と根拠

ORDレコード
ord-a7c9f4bc7cf1419f8ffeeeb820bb018c
出典データセット
uspto-grants-2003_09
特許番号
US06627651B1

反応ノート

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