2-Nitropropane → 2-Methyl-1-(naphthalen-2-YL)-2-nitropropan-1-OL

HRID 895867ノート

反応式

HRID 895867 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N+:19]([CH:22]([CH3:24])[CH3:23])([O-:21])=[O:20].[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[CH:35]=[O:36].C([Si](C)(C)Cl)(C)(C)C>O1CCCC1.C(N(CC)CC)C>[CH3:23][C:22]([N+:19]([O-:21])=[O:20])([CH3:24])[CH:35]([C:26]1[CH:27]=[CH:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=1)[OH:36]

参加物

7

反応物 4

HCID 3982-NitropropaneHCID 62012-NaphthalenecarboxaldehydeHCID 28928tert-Butyldimethylsilyl chlorideHCID 2724141Tetrabutylammonium Fluoride

生成物 1

HCID 126400842-Methyl-1-(naphthalen-2-YL)-2-nitropropan-1-OL

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To tetrabutylammonium fluoride 3 hydrate (2.41 g) was added tetrahydrofuran (20 ml) and the mixture was ice-cooled. To the mixture were added 2-nitropropane (2.7 ml), 2-naphthaldehyde (3.12 g) and triethylamine (2.8 ml) under an argon atmosphere. To the mixture was added a solution of tert-butyldimethylchlorosilane (4.51 g) in tetrahydrofuran (20 ml). The resulting mixture was stirred for 40 min while allowing to warm to room temperature from ice-cooling. After removing insoluble matter by filtration, the filtrate was poured into a solution (500 ml) of diethyl ether-n-hexane=1:3 and the mixture was washed twice with water (40 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to crystallization from n-hexane to give the title compound (3.78 g).

後処理

  1. temperaturecooled
  2. temperaturecooling
  3. customAfter removing insoluble matter
  4. filtrationby filtration
  5. additionthe filtrate was poured into a solution (500 ml) of diethyl ether-n-hexane=1:3
  6. washthe mixture was washed twice with water (40 ml)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was subjected to crystallization from n-hexane

出典と根拠

ORDレコード
ord-2f2e9ac4566b444c9eb2e1c7e48b1980
出典データセット
uspto-grants-2005_07
特許番号
US06916956B2

反応ノート

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