tert-Butanol → HCID 67043319, Verbindung
Reaktionsgleichung
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]([F:18])([F:17])[C:8]1[CH:16]=[CH:15][C:11](C(O)=O)=[CH:10][N:9]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C>>[C:1]([O:5][C:41](=[O:26])[NH:38][C:11]1[CH:10]=[N:9][C:8]([C:7]([Cl:6])([F:17])[F:18])=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]Komponenten
5
Versuchsvorschrift
Under a nitrogen atmosphere, a solution of tert-butanol (100 ml), molecular sieve powder (4 angstrom) (23 g) and triethylamine was prepared (9.36 ml). After stirring for 5 minutes at ambient temperature, the compound obtained in Step A (10 g) was added, followed by diphenyl phosphoryl azide (16.3 g). The reaction mixture was heated to reflux for 3 hours and then filtered on Celite®. The reaction mixture was poured into water and extracted several times with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane/ethyl acetate 5:1) afforded [6-(chlorodifluoromethyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (10.6 g). MS (ES+) 279/281 (MH+); 1H NMR (400 MHz, CDCl3) 1.55 (s, 9H), 7.52 (d, 1H), 8.19 (m, 1H), 8.47 (d, 1H).