Chloroform → HCID 12398838, Verbindung

HRID 329329

Reaktionsgleichung

Reaktionsgleichung von HRID 329329
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14]([OH:16])=[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.C(Cl)(Cl)Cl.S(Cl)(Cl)=O.CN(C)C=O>CCCCCC.CCOCC>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:17])[C:14]([O:16][CH2:8][CH2:2][CH:3]([CH3:21])[CH3:4])=[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

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

Produkt 1

HCID 12398838HCID 12398838, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584099Diethylether hexaneLösungsmittel

Versuchsvorschrift

1.0 G. of (5-oxo-5H-dibenzo[a,d]cyclohepten-2yl)-propionic acid is dissolved in 25 ml. of chloroform, and 1 ml. of thionyl chloride and 0.1 ml. of dimethylformamide are added thereto. The mixture is left for 3 hrs., then evaporated to dryness. The residue is dissolved in 20 ml. of benzene and evaporated to dryness. 0.5 G of the residue is dissolved in 5 ml. of acetonitrile containing 1.0 ml. of isopentylalcohol and 1.0 ml. of triethylamine. The mixture is left at room temperature for 16 hrs., then poured into water. The solution is extracted with ether and the extract washed with water, dilute hydrochloric acid, aqueous sodium carbonate, dried and evaporated to yield the crude product which is dissolved in hexane:ether (1:1), the solution passes through silica gel, and the eluant evaporated to afford isopentyl (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate [an oil; n.m.r. spectrum in deuterochloroform relative to tetramethylsilane: 0.87 (doublet CH[CH3 ]2 ; 1.57 (doublet, CHCH3) and 7.23 ppm (singlet 10H,11H); mass spectrum: 348(M+), 278, 234, 233, 205].

Aufarbeitung

  1. custom, then evaporated to dryness
  2. dissolutionThe residue is dissolved in 20 ml
  3. customof benzene and evaporated to dryness
  4. dissolution0.5 G of the residue is dissolved in 5 ml
  5. waitThe mixture is left at room temperature for 16 hrs
  6. addition, then poured into water
  7. extractionThe solution is extracted with ether
  8. washthe extract washed with water, dilute hydrochloric acid, aqueous sodium carbonate
  9. customdried
  10. customevaporated
  11. customto yield the crude product which
  12. customthe eluant evaporated

Quellen und Nachweise

ORD-Eintrag
ord-a5c532e47f134f4da172c6be943a783d
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04020094

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