반응 #48326

반응 방정식

7-Hydroxy-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one

triphenylphosphine

diisopropyl azodicarboxylate

(r)-(−)-3-hydroxytetrahydrofuran

HCl

→

(S)-3,3-dimethyl-7-(tetrahydrofuran-3-yloxy)-3,4-dihydronaphthalen-1(2H)-one

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출the mixture was extracted 3 times with EtOAc

실험 절차

7-Hydroxy-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one (0.95 g, 4.99 mmol) was dissolved in 30 ml DCMand triphenylphosphine (1.96 g, 7.49 mmol) and diisopropyl azodicarboxylate (1.23 ml, 6.24 mmol) and (r)-(−)-3-hydroxytetrahydrofuran (0.600 ml, 7.49 mmol) was added. The mixture was stirred over night. 0.5M HCl (aq.) was added and the mixture was extracted 3 times with EtOAc. Glass col. Chrom. (5-30% EtOAc in Hex.) provided (S)-3,3-dimethyl-7-(tetrahydrofuran-3-yloxy)-3,4-dihydronaphthalen-1(2H)-one as a yellow oil. MS m/z: 261.1 (M+1).

출처