Acetic Acid → (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

HRID 1087662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087662
C[Li].[CH:3]1([C@:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([OH:13])[C:10]([OH:12])=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:20](O)(=O)C.O>CCOCC.C1COCC1>[CH:3]1([C@@:9]([OH:13])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:12])[CH3:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 777377Cyclohexylphenylglycolic acid, (-)-HCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 15030055(R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 315 ml of 1.4M CH3Li (0.44 mole) in ether and 750 ml of THF at room temperature was added a solution of 26 g (0.11 mole) of (R)-cyclohexylmandelic acid, prepared by the method of R. B. Barlow, F. M. Franks, and J. D. M. Pearson, J. Med. Chem., 16, 439 (1973), in THF. Following the addition, the mixture was stirred at room temperature for 3.5 hours and then brought to reflux for 3 hours. The mixture was cooled and then added dropwise to a mixture of 300 ml of glacial acetic acid and 700 ml of water. This mixture was extracted with ether, the organic layer was separated, washed with water and saturated aqueous sodium bicarbonate, dried, and the solvent removed. The mixture was distilled to give 20 g of clear oil (bp 120° C., 0.1 mm Hg), NMR (chloroform-d) δ7.5(m, 5H), 4.5(S, 1H), 2.4(t, 1H), 2.0(s, 3H), 1.9-1.0(m, 10H).

Aufarbeitung

  1. customprepared by the method of R
  2. additionthe addition
  3. temperatureto reflux for 3 hours
  4. temperatureThe mixture was cooled
  5. extractionThis mixture was extracted with ether
  6. customthe organic layer was separated
  7. washwashed with water and saturated aqueous sodium bicarbonate
  8. customdried
  9. customthe solvent removed
  10. distillationThe mixture was distilled

Quellen und Nachweise

ORD-Eintrag
ord-d1c5336e13e64664b508272c15d968ac
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05036107

Notizen zur Reaktion

Wird geladen…