[CH2:1]([C@@H:3]1[O:5][CH2:4]1)Cl.[CH3:6][C:7]1([CH3:18])[CH2:16][CH2:15][CH2:14][C:13]2[CH:12]=[C:11]([OH:17])[CH:10]=[CH:9][C:8]1=2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:6][C:7]1([CH3:18])[CH2:16][CH2:15][CH2:14][C:13]2[CH:12]=[C:11]([O:17][CH2:1][C@@H:3]3[CH2:4][O:5]3)[CH:10]=[CH:9][C:8]1=2To a mixture of (R)-epichlorohydrin (2.2 g, 23.8 mmol) and 5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol (2.1 g, 11.9 mmol) in acetone (30 ml) was added potassium carbonate (1.65 g, 11.9 mmol). The mixture was stirred at 45° C. for 7 days. The reaction mixture was then concentrated. The residue was partitioned between ethyl acetate and water and extracted twice with ethyl acetate. The organic extracts were combined and washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by flash chromatography (silica, methylene chloride/heptane) to give 1.84 g (67%) of (S)-2-(5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxymethyl)-oxirane.
Loading…
