Acetic Acid → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal

HRID 1283677ノート

反応式

HRID 1283677 の反応式
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.O.N(C(NC1C=CC=CC=1)C)C1C=CC=CC=1.C(O)(=O)C>COCCOCCOC.CO>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[CH:14]=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 15852811DianilinoethaneHCID 203106912-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionyl chloride

生成物 1

HCID 214093832-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8150Diglyme溶媒2 回

実験手順

0.25 G. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)-propionyl chloride (as prepared in Preparation 10 above) is dissolved in 4 ml. of diglyme and the solution cooled to -78°C. 3.5 Ml. of 0.045 molar lithium aluminum tri-tertiary butoxy hydride in diglyme is added, in 0.5 ml. portions over the course of 1 hour, to this solution. The mixture is warmed to room temperature and poured into water and extracted with ether. The extract is washed, dried and evaporated to give a crude product to which is added a solution of 0.106 g. of dianilinoethane and 0.072 g. of acetic acid in 5 ml. of methanol. The mixture is left for 1 hour than decanted from the insoluble product, α-(1,3-diphenyl-2-imidazolidinyl) 2-ethyl-5-oxo-5H-dibenzo[a,d]cycloheptene [a gum; nmr spectrum in deuterochloroform relative to tetramethylsilane: 1.47 (doublet, CHCH3), 5.77 (singlet, N-CH-N) acid 6.90 ppm (singlet, 10H, 11H). This compound is dissolved in 10 ml. of ether and the solution shaken with dilute hydrochloric acid. The ethereal layer is dried and evaporated to give 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal [a gum; nmr spectrum in deuterochloroform relative to tetramethylsilane: 0.98 (doublet, CHCH3), 3.78 (quartet, CHCH3), 7.02 (singlet, 10H, 11H) and 9.72 ppm (doublet, CHO); mass spectrum: 262 (M+) 233, 205] .

後処理

  1. customover the course of 1 hour
  2. extractionextracted with ether
  3. washThe extract is washed
  4. customdried
  5. customevaporated
  6. customto give a crude product to which
  7. additionis added a solution of 0.106 g
  8. customthan decanted from the insoluble product, α-(1,3-diphenyl-2-imidazolidinyl) 2-ethyl-5-oxo-5H-dibenzo[a,d]cycloheptene [a gum
  9. dissolutionThis compound is dissolved in 10 ml
  10. customThe ethereal layer is dried
  11. customevaporated

出典と根拠

ORDレコード
ord-f53dbed02c7c49e79c130b6b9480a3d6
出典データセット
uspto-grants-1976_08
特許番号
US03975540

反応ノート

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