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Diethyl Ether → 5-Hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

HRID 4672
ノート
印刷プレビュー

反応式

HRID 4672 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C:13]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]=[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)[C:14]=1[C:34](OC)=[O:35]>O1CCCC1>[OH:35][CH2:34][C:14]1[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)=[N:16][C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:18][C:13]=1[CH3:12]
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 3283Diethyl EtherHCID 15147475Methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylateHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 103361765-Hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine収率 72.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of lithium aluminum hydride (12.24 g) in a mixture of dry tetrahydrofuran (180 ml) and diethyl ether (360 ml) was dropwise added a solution of methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (45 g) in dry tetrahydrofuran (180 ml) under cooling at -50°~-40° C. The excess lithium aluminum hydride was decomposed by a careful addition to ice water. The separated organic layer was washed with 15% sulfuric acid (400 ml) and extracted with ethyl acetate (1 l). The organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride successively and concentrated in vacuo. The residue was recrystallized from diethyl ether to give 5-hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (30 g).

後処理

  1. temperatureunder cooling at -50°~-40° C
  2. washThe separated organic layer was washed with 15% sulfuric acid (400 ml)
  3. extractionextracted with ethyl acetate (1 l)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride successively
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-75a16eec411946899f802c923c0a7c7d
出典データセット
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04727073

反応ノート

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