HCID 58677920, Verbindung → HCID 49762843, Verbindung

HRID 2102225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2102225
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](N(OC)C)=[O:11])=[CH:4][CH:3]=1.[CH:16]1([Mg]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 58677920HCID 58677920, VerbindungHCID 178419651HCID 178419651, Verbindung

Produkt 1

HCID 49762843HCID 49762843, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of 25.02 g 3-(4-Bromophenyl)-N-methoxy-N-methylpropanamide from Step A above in 500 mL anhydrous ether cooled in an ice bath was added 115 mL 2 M cyclohexylmagnesium bromide in ether over 30 minutes. The cooling bath was removed after finishing addition. After 75 minutes, an additional 30 mL 2 M cyclohexylmagnesium bromide in ether was added. The reaction mixture was stirred for 40 minutes and poured into a mixture containing 500 mL ether, 500 mL cold water, 200 mL saturated brine, and 175 mL 2 N HCl. The layers were separated. The aqueous layer was extracted with 4×75 mL ether. The combined ether solution was washed with 200 mL 1:1 5% NaHCO3 and saturated brine followed by 200 mL saturated brine, dried over anhydrous Na2SO4, and evaporated to give a crude product. It was purified on silica gel using 20-100% EtOAc in hexanes and re-purified using 5-10% EtOAc in hexanes to give the title compound as yellow oil. 1H NMR (CDCl3, 500 MHz) δ 7.39˜7.42 (m, 2H), 7.06˜7.09 (m, 2H), 2.84˜2.87 (m, 2H), 2.74˜2.78 (m, 2H), 2.32 (tt, J=3.3 & 11.3 Hz, 1H), 1.76˜1.84 (m, 4H), 1.65˜1.70 (m, 1H), 1.15˜1.36 (m, 5H).

Aufarbeitung

  1. customThe cooling bath was removed
  2. additionaddition
  3. additionan additional 30 mL 2 M cyclohexylmagnesium bromide in ether was added
  4. additionpoured into a mixture
  5. additioncontaining 500 mL ether, 500 mL cold water, 200 mL saturated brine, and 175 mL 2 N HCl
  6. customThe layers were separated
  7. extractionThe aqueous layer was extracted with 4×75 mL ether
  8. washThe combined ether solution was washed with 200 mL 1:1 5% NaHCO3 and saturated brine
  9. dry with materialdried over anhydrous Na2SO4
  10. customevaporated
  11. customto give a crude product
  12. customIt was purified on silica gel using 20-100% EtOAc in hexanes
  13. customre-purified

Quellen und Nachweise

ORD-Eintrag
ord-6e04392956d54da0bd75f83241087ee3
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572922B2

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