Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methylbenzonitrile

HRID 1951395ノート

反応式

HRID 1951395 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[CH3:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16].C(O)(=O)C.N1CCCCC1>ClCCl>[C:15]([C:14]([C:13](=[O:18])[CH3:12])=[CH:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1])(=[O:17])[CH3:16]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 109096954-Formyl-3-methylbenzonitrile

生成物 1

HCID 596030304-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methylbenzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

950 mg (6.54 mmol) of 3-methyl-4-formylbenzonitrile [S. Levesque et al., Bioorg. Med. Chem. Lett. 11, 3161-3164 (2000], 655.2 mg (6.544 mmol) of 2,4-pentanedione, 589.5 mg (9.82 mmol) of acetic acid and 111.5 mg (1.31 mmol) of piperidine are dissolved in 35 ml of dichloromethane and heated under reflux with an inverse water trap overnight. Cooling is followed by washing twice with water, and the organic phase is dried with magnesium sulfate. The solvent is removed in a rotary evaporator and the residue is purified by column chromatography (silica gel, mobile phase: initially dichloromethane, then isohexane/ethyl acetate 3:1). After concentration of the product fractions, the residue is crystallized from diethyl ether and dried under high vacuum. 1.12 g (75.3% of theory) of the title compound are obtained.

後処理

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap overnight
  3. temperatureCooling
  4. washby washing twice with water
  5. dry with materialthe organic phase is dried with magnesium sulfate
  6. customThe solvent is removed in a rotary evaporator
  7. customthe residue is purified by column chromatography (silica gel, mobile phase
  8. customAfter concentration of the product fractions, the residue is crystallized from diethyl ether
  9. customdried under high vacuum

出典と根拠

ORDレコード
ord-ffc25bb006974dd58b30decbfe449b09
出典データセット
uspto-grants-2013_03
特許番号
US08404709B2

反応ノート

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