Acetic Acid → HCID 131731401, Verbindung

HRID 1026648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026648
[Cl:1][C:2]1[C:14]2[CH2:13][CH2:12][C@@:11]3([CH3:15])[C@H:7]([CH2:8][N:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O)(=[O:23])C.[O-2].[Ce+4].[O-2].Br([O-])(=O)=O.[Na+]>O.O1CCOCC1>[Cl:1][C:2]1[C:14]2[C:13](=[O:23])[CH2:12][C@@:11]3([CH3:15])[C@H:7]([CH2:8][N:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 10219615Ceric oxideHCID 23668195Sodium BromateHCID 131731400HCID 131731400, Verbindung

Produkt 1

HCID 131731401HCID 131731401, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

cis-Ethyl 6-chloro-3a-methyl-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (5.55 mmol, 1630 mg) was dissolved in water (33 ml), acetic acid (8.25 ml) and 1,4-dioxane (8.25 ml). Cerium(IV) oxide (1.276 mmol, 220 mg) and sodium bromate (5.55 mmol, 837 mg) were added and the reaction mixture was heated to 95° C. for 3 hours. The reaction mixture was cooled to rt, diluted with water (30 ml) and extracted with ether. The organic extracts were dried over magnesium sulphate, filtered and the solvent removed in vacuo to give to give a crude residue that was purified by silica column chromatography (eluting with 0-60% ethyl acetate in heptane) to give cis-ethyl 6-chloro-3a-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (673 mg), m/z=308.7 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with ether
  3. dry with materialThe organic extracts were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give
  7. customto give a crude residue that
  8. customwas purified by silica column chromatography (eluting with 0-60% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-5a98790d329e4aafbe81b68d837e4dbc
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729274B2

Notizen zur Reaktion

Wird geladen…