Chloroform → HCID 58575621, Verbindung

HRID 1807848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807848
[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(Cl)(Cl)Cl.Cl[C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1Cl)[CH2:20]N=C([O-])C(Cl)(Cl)Cl.FC(F)(F)S(O)(=O)=O>CCCCCC>[CH2:20]([O:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:19]1[CH:28]=[CH:29][CH:30]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 62406Trifluoromethanesulfonic acidHCID 2724648rel-Ethyl (1R,2S)-2-hydroxycyclopentanecarboxylateHCID 86660663HCID 86660663, Verbindung

Produkt 1

HCID 58575621HCID 58575621, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a mixture of 1.00 g of ethyl cis-2-hydroxy-1-cyclopentane carboxylate, 8.00 mL of chloroform, 16.0 mL of normal hexane, and 1.77 mL of 3,4-dichlorobenzyl-2,2,2-trichloroacetimidate was added 0.335 mL of trifluoromethane sulfonic acid at room temperature under a nitrogen atmosphere, followed by stirring for 3 hours. The insoluble materials were removed by filtration, and to the filtrate was added a saturated aqueous sodium hydrogen carbonate solution under ice-cooling to adjust the pH to about 7, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 1.27 g of ethyl cis-2-benzyloxy-1-cyclopentane carboxylate as a colorless oily substance.

Aufarbeitung

  1. customThe insoluble materials were removed by filtration
  2. additionto the filtrate was added a saturated aqueous sodium hydrogen carbonate solution under ice-
  3. temperaturecooling
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e82a2cd911f84b47a463d2156543df07
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357688B2

Notizen zur Reaktion

Wird geladen…