Water → tert-Butyl 7-ethoxynaphthalen-1-ylcarbamate

HRID 30528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30528
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[CH:17]=[C:16]([OH:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:27][CH3:28].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:27][CH3:28])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Produkt 1

HCID 59731041tert-Butyl 7-ethoxynaphthalen-1-ylcarbamateAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Next, to a mixture of N-t-butoxycarbonyl-8-amino-2-naphthol (64.0 g, 247 mmol) and Cesium carbonate (161 g, 493 mmol) in 300 mL anhydrous DMF was added iodoethane (42.3 g, 272 mmol) at room temperature. The mixture was stirred at 60° C. for 2 hours. Water was added to the mixture, and the product was extracted with ethylacetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. To the obtained residue was added diisopropyl ether and the precipitate was collected and dried to afford (7-ethoxy-naphthalen-1-yl)-carbamic acid t-butyl ester (47.9 g, 67.5% yield).

Aufarbeitung

  1. extractionthe product was extracted with ethylacetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionTo the obtained residue was added diisopropyl ether
  7. customthe precipitate was collected
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e7dcb86d6b4f47fd9615e98bc941b719
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423175B2

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