Reaktion #538149

Reaktionsgleichung

(2-isocyanatocyclopropyl)benzene

DBU

1-chloro-3-phenylhex-5-en-3-ol

→

6-allyl-6-phenyl-3-(2-phenylcyclopropyl)-1,3-oxazinan-2-one

Ausbeute 7.2%

Lösungsmittel

THF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed overnight
2. 2
   Waschenwashed with 1 N HCl (2×15 mL)
3. 3
   ExtraktionThe aqueous phase was extracted with EtOAc
4. 4
   WaschenThe combined organic layers were washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto give crude product, which
9. 9
   Sonstigewas purified by preparative TLC

Vorschrift

To a solution of (2-isocyanatocyclopropyl)benzene (800 mg, 5.03 mmol) in THF (15 mL) was added DBU (1.61 g, 10.48 mmol) and 1-chloro-3-phenylhex-5-en-3-ol (880 mg, 4.19 mmol), and the mixture was refluxed overnight. The solution was diluted with EtOAc, and washed with 1 N HCl (2×15 mL). The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give crude product, which was purified by preparative TLC to afford 6-allyl-6-phenyl-3-(2-phenylcyclopropyl)-1,3-oxazinan-2-one (100 mg, 6%). 1H NMR (CDCl3): 1.05-1.21 (m, 3H), 1.36-1.42 (m, 1H), 2.13-2.34 (m, 1H), 2.39-2.61 (m, 2H), 2.92-3.15 (m, 1H), 3.76-4.01 (m, 1H), 4.95-5.10 (m, 2H), 5.42-5.73 (m, 1H), 6.95-6.99 (m, 1H), 7.10-7.24 (m, 10H).

Quelle