Hydrochloric Acid → HCID 67226130, Verbindung

HRID 1518888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518888
[H-].[Na+].[Br-].[Br:4][C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:32]1[CH2:37][CH2:36][N:35]([C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([O:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:39]=2)[CH2:34][CH2:33]1.Cl>CS(C)=O>[Br:4][C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[CH:7]=[C:32]1[CH2:33][CH2:34][N:35]([C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([O:48][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH:39]=2)[CH2:36][CH2:37]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 11733967Phosphonium, [(2-bromophenyl)methyl]triphenyl-, bromideHCID 67226770HCID 67226770, Verbindung

Produkt 1

HCID 67226130HCID 67226130, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

Dimethylsulfoxide (22.88 mL) with sodium hydride (0.332 g) was heated to 70° C. for 1 hour, then cooled to room temperature and (2-bromobenzyl)triphenylphosphonium bromide (3.40 g) was added in several portions, and then stirred at room temperature for 1 hour. A solution of methyl 4-(4-oxopiperidin-1-yl)-2-phenoxybenzoate (1.8 g) in dimethylsulfoxide (5.20 mL) was then added and the reaction was heated to 70° C. over the weekend. The reaction was acidified with 1M aqueous HCl solution and extracted with ether. The combined extracts were washed thoroughly with water and brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography eluting with 0-20% ethyl acetate in hexanes.

Aufarbeitung

  1. temperaturethe reaction was heated to 70° C. over the weekend
  2. extractionextracted with ether
  3. washThe combined extracts were washed thoroughly with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography
  8. washeluting with 0-20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3fe122cb47e5462b9e978712e246b274
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09072748B2

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