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

HRID 4672
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HRID 4672 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 15147475Methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylateHCID 21226445Aluminium lithium hydride2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-75a16eec411946899f802c923c0a7c7d
출처 데이터셋
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04727073

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