Ethanol → N-(6-fluoro-2-naphthyl)carbamic acid ethyl ester

HRID 1270767

Reaktionsgleichung

Reaktionsgleichung von HRID 1270767
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](C(O)=O)[CH:6]=[CH:5]2.C([N:17]([CH2:20]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1.[CH2:39]([OH:41])[CH3:40]>O1CCOCC1>[CH2:39]([O:41][C:20](=[O:29])[NH:17][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH:8]=1)[CH3:40]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27827886-Fluoro-2-naphthoic acid

Produkt 1

HCID 68804469N-(6-fluoro-2-naphthyl)carbamic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of 6-fluoro-2-naphthoic acid (450 mg, 2.37 mmol) and triethylamine (0.66 mL, 4.73 mmol) in 1,4-dioxane (30 mL) at room temperature, is added DPPA (0.77 mL, 3.55 mmol). After stirring at room temperature for 2.5 hours, ethanol (1.38 mL, 23.7 mmol) is added and the reaction is heated to reflux temperature for 12 hours. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (3:1 hexanes/EtOAc) gives N-(6-fluoro-2-naphthyl)carbamic acid ethyl ester as an oil.

Aufarbeitung

  1. temperaturethe reaction is heated
  2. temperatureto reflux temperature for 12 hours
  3. temperatureAfter cooling to room temperature
  4. customthe mixture is partitioned between EtOAc and water
  5. washThe organic layer is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by rotary evaporator
  8. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-9889c43ee7a0494f9237e9f5a932a7c9
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202364B2

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