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

HRID 1951398ノート

反応式

HRID 1951398 の反応式
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1)=O.[CH3:15][C:16](=[O:21])[CH2:17][C:18](=[O:20])[CH3:19].C(O)(=O)C.N1CCCCC1>ClCCl>[C:18]([C:17]([C:16](=[O:21])[CH3:15])=[CH:1][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]#[N:14])=[CH:5][CH:4]=1)(=[O:20])[CH3:19]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 124330094-Formylnaphthalene-1-carbonitrile

生成物 1

HCID 596030144-(2-Acetyl-3-oxobut-1-en-1-yl)-1-naphthonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

240 mg (1.33 mmol) of 4-formyl-1-naphthonitrile, 132.6 mg (1.33 mmol) of 2,4-pentanedione, 119.3 mg (1.99 mmol) of acetic acid and 22.6 mg (0.27 mmol) of piperidine are dissolved in 20 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). The residue after concentration of the product fractions is crystallized from diethyl ether and dried under high vacuum. 340 mg (97.5% 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. customThe residue after concentration of the product fractions is crystallized from diethyl ether
  9. customdried under high vacuum

出典と根拠

ORDレコード
ord-5158365156f24d47a7465fac54d0aa45
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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