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Hydrogen Peroxide → 3-(3,4-dimethoxybenzyl)-6-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

HRID 1022509
ノート
印刷プレビュー

反応式

HRID 1022509 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:18]=[CH2:19])[CH:14]=2)[N:9]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:8]1=[O:26].[OH-:32].[Na+].OO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][CH2:19][OH:32])[CH:14]=2)[N:9]([CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:8]1=[O:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 497631873-(3,4-dimethoxybenzyl)-6-ethenyl-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

生成物 1

HCID 497631863-(3,4-dimethoxybenzyl)-6-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

0.95 ml of a 1N solution of BH3-THF complex in THF is added, at 0° C., to a mixture of 0.1 g of 3-(3,4-dimethoxybenzyl)-6-ethenyl-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione in 2 ml of THF. The reaction medium is allowed to warm to room temperature and is stirred for 1 hour. 2 ml of 1N sodium hydroxide and then 2 ml of 30% aqueous hydrogen peroxide solution are added. The resulting mixture is refluxed for 1 hour and then extracted with DCM. The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (80/20, v/v) to (40/60) to give 0.057 g of the expected product.

後処理

  1. temperatureThe resulting mixture is refluxed for 1 hour
  2. extractionextracted with DCM
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluting with a DCM/EtOAc mixture from (80/20

出典と根拠

ORDレコード
ord-949b954c0c464c88a146c329465fbd50
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722659B2

反応ノート

読み込み中…

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