3-Nitrobenzaldehyde → Ethyl 4,4,4-trichloro-2-(3-nitrophenylmethylene)-3-oxobutanoate

HRID 364954

反応式

HRID 364954 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[Cl:12][C:13]([Cl:23])([Cl:22])[C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].N1CCCCC1.C(O)(=O)CCCCC>C1(C)C=CC=CC=1>[Cl:12][C:13]([Cl:22])([Cl:23])[C:14](=[O:21])[C:15](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

参加物

6

反応物 4

HCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 8892Hexanoic AcidHCID 77294Ethyl 4,4,4-trichloro-3-oxobutyrate

生成物 1

HCID 54196727Ethyl 4,4,4-trichloro-2-(3-nitrophenylmethylene)-3-oxobutanoate収率 28.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

3-Nitrobenzaldehyde (7.55 g, 50 mmoles), ethyl 4,4,4-trichloro-3-oxobutanoate (18.33 g, 59.5 mmoles), piperidine (0.66 ml) and hexanoic acid (0.33 ml) were heated at reflux in toluene (130 ml) for 48 hours using a Dean and Stark apparatus. The mixture was cooled, evaporated to dryness in vacuo and crystallised by trituration with ethyl acetate/petroleum ether (60°-80°). Recrystallisation from 2-propanol gave the sub-title compound (5.3 g) mp 105.5°-7°.

後処理

  1. temperatureThe mixture was cooled
  2. customevaporated to dryness in vacuo
  3. customcrystallised by trituration with ethyl acetate/petroleum ether (60°-80°)
  4. customRecrystallisation from 2-propanol

出典と根拠

ORDレコード
ord-0f5d9b338d8f460eab0a9a6edb5f6d22
出典データセット
uspto-grants-1986_08
特許番号
US04607041

関連ノート

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