3-Nitrobenzaldehyde → Methyl 4-[2-(3-nitrophenyl)vinyl]benzoate

HRID 1160384

反応式

HRID 1160384 の反応式
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].[N+:32]([C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH:38]=O)([O-:34])=[O:33].C1CC23[N+](=[N-])C(CCC2)=C3C1>C(#N)C>[N+:32]([C:35]1[CH:36]=[C:37]([CH:38]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:31][CH:30]=2)[CH:40]=[CH:41][CH:42]=1)([O-:34])=[O:33]

参加物

5

反応物 3

HCID 74493-NitrobenzaldehydeHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 219219891,5-Diazobicyclo(4.3.0)non-5-ene

生成物 1

HCID 68690726Methyl 4-[2-(3-nitrophenyl)vinyl]benzoate収率 95%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

71.2 g of 4-methoxycarbonylbenzyltriphenylphosphonium bromide and 23 g (0.15 M) of 3-nitrobenzaldehyde are added to 360 ml of acetonitrile in a 1000 ml reactor. 19 ml (0.15 M) of 1,5-diazobicyclo[4.3.0]non-5-ene (DBN) are then added and the reaction medium is then refluxed with stirring for 1 hour. The solvent is then evaporated off and the residue obtained is then purified by chromatography on silica, using dichloromethane as eluent. After evaporation, 41.6 g of a white solid are obtained (yield: 95%).

後処理

  1. temperaturethe reaction medium is then refluxed
  2. customThe solvent is then evaporated off
  3. customthe residue obtained
  4. customis then purified by chromatography on silica
  5. customAfter evaporation, 41.6 g of a white solid
  6. customare obtained (yield: 95%)

出典と根拠

ORDレコード
ord-db25ae22fe1a45c58be3ca0a56c10117
出典データセット
uspto-grants-2010_10
特許番号
US07816397B2

関連ノート

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