Pyridine → 2-Nitrobenzeneacetaldehyde

HRID 485284

反応式

HRID 485284 の反応式
FC(F)(F)C(O)=O.N1C=CC=CC=1.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][OH:25])([O-:16])=[O:15].C1CCC(N=C=NC2CCCCC2)CC1.O.O.C(O)(=O)C(O)=O>C(OCC)(=O)C.C1C=CC=CC=1.C(OCC)(=O)C.C1C=CC=CC=1.CS(C)=O>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH:24]=[O:25])([O-:16])=[O:15]

参加物

10

反応物 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 270542-Nitrophenethyl alcoholHCID 61373Oxalic acid dihydrate

生成物 1

HCID 108447642-Nitrobenzeneacetaldehyde収率 81%

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒HCID 21583983Benzene ethyl acetate溶媒

実験手順

Trifluoroacetic acid (1.31 ml, 17 mmols) and 2.7 ml (33.3 mmols) of pyridine were added to a mixture of 5.51 g (33.3 mmols) of 2-(2-nitrophenyl)ethanol, 50 ml of dimethyl sulfoxide, 50 ml of benzene and 21 g (0.1 mol) of DCC. After stirring the mixture at room temperature for 4 hours, 300 ml of aqueous solution of 8.82 g (70 mmols) of oxalic acid dihydrate was added thereto. The resulting mixture was stirred at room temperature for 30 minutes and diluted with 500 ml of ethyl acetate. The organic layer was separated off, washed with saturated NaCl, dried over Na2SO4 and concentrated to obtain a yellow oil. The oil was subjected to silica gel column chromatography (95:5 benzene-ethyl acetate) to obtain 2-nitrophenylacetoaldehyde in the form of an unstable oil in an amount of 4.50 g (yield 81%).

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. customThe organic layer was separated off
  3. washwashed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain a yellow oil

出典と根拠

ORDレコード
ord-d91480da54914daba6ee0526fbba308a
出典データセット
uspto-grants-1985_08
特許番号
US04536391

関連ノート

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