反应详情

A solution of 50 (160 mg, 0.257 mmol) in anhydrous CH2Cl2 (0.3 mL) was cooled in an ice bath under argon for 10 min. TiCl4 (25 μL) was added, and the resulting mixture was stirred for 10 min. 2-(Trimethylsilyloxy)prop-1-ene (33.4 mg, 0.257 mmol, 0.43 μL) was added. Stirring was continued for 20 min. The reaction mixture was diluted with ice-cold water. CH2Cl2 was added, and the phases were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4). Concentration of the sample under reduced pressure yielded a pale yellow oil, which was purified by column chromatography [silica, hexanes/ethyl acetate (10:1→3:1)] affording a colorless oil (18 mg, 10%): 1H NMR δ 1.04 (s, 18H), 1.85-1.89 (m, 4H), 2.18 (s, 3H), 2.61 (s, 2H), 3.65 (m, 4H), 7.37-6.42 (m, 12H), 7.65-7.67 (m, 8H).

1. stirringStirring
2. waitwas continued for 20 min
3. additionThe reaction mixture was diluted with ice-cold water
4. customthe phases were separated
5. extractionThe aqueous layer was extracted with CH2Cl2
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. customConcentration of the sample under reduced pressure yielded a pale yellow oil, which
8. customwas purified by column chromatography [silica, hexanes/ethyl acetate (10:1→3:1)]