Citric Acid → 4-Hydroxy-2-(4-hydroxybenzyl)-3-methyl-5-propylbenzofuran

HRID 1534200ノート

反応式

HRID 1534200 の反応式
C(S)C.[H-].[Na+].[OH:6][C:7]1[C:12]2[C:13]([CH3:25])=[C:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)[O:15][C:11]=2[CH:10]=[CH:9][C:8]=1[CH2:26][CH2:27][CH3:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[OH:6][C:7]1[C:12]2[C:13]([CH3:25])=[C:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[O:15][C:11]=2[CH:10]=[CH:9][C:8]=1[CH2:26][CH2:27][CH3:28]

参加物

6

反応物 4

HCID 311Citric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

生成物 1

HCID 145797614-Hydroxy-2-(4-hydroxybenzyl)-3-methyl-5-propylbenzofuran収率 92.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Under nitrogen atmosphere, ethanethiol (4.9 g; 80 mmoles) was added dropwise over 5 minutes to a mixture of 99% sodium hydride (1.9 g; 80 mmoles) in dimethylformamide (100 ml). After stirring for 15 minutes, a solution of 4-hydroxy-2-(4-methoxybenzyl)-3-methyl-5-propylbenzofuran (2.4 g; 8 mmoles) in dimethylformamide (5 ml) was added in one portion. The mixture was refluxed for 2 hours, cooled, acidified with 20% citric acid solution and extracted with ether. The ether solution was washed with water, dried (Na2SO4), filtered, concentrated, and chromatographed to obtain 2.2 g of the title compound as an oil which crystallized from an ether-hexane mixture.

後処理

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed

出典と根拠

ORDレコード
ord-821a8a9a5ed94ca4bc85706895bfb5a8
出典データセット
uspto-grants-1992_02
特許番号
US05087638

反応ノート

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