反应详情

Diethyl azodicarboxylate (0.059 mL, 65 mg, 0.37 mmol) was added to a solution of 2-phenyl-3-(tert-butyldimethylsilyloxy)-1-propanol (100 mg, 0.375 mmol), N-methylbenzenesulfonamide (77 mg, 0.45 mmol), and triphenylphosphine (98.4 mg, 0.38 mmol) in 1.0 mL of dry THEF, and the mixture was stirred 4 h at room temperature. Additional triphenylphosphine (48 mg, 0.18 mmol) and diethyl azodicarboxylate (0.030 mL, 33 mg, 0.19 mmol) were added and stirring was continued overnight at room temperature. After concentrating in vacuo, the residue was dissolved in 50 mL of dichloromethane and washed with 25 mL of 10% aqueous sodium hydroxide and 25 mL of brine. The organic layer was dried over sodium sulfate, decanted, and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with 5% ethyl ether in hexane to give 83 mg of the title compound as a colorless syrup. 1NMR (400 MHz, CDCl3): δ 7.73 (d, 2H, J=7 Hz), 7.57 (tt, 1H, J=7, 1 Hz), 7.49 (t, 2H, J=7 Hz), 7.33-7.20 (m, 5H), 3.84 (dd, 1H, J=10, 6 Hz), 3.77 (dd, 1H, J=10, 6 Hz), 3.48 (dd, 1H, J=13, 7 Hz), 3.20 (dd, 1H, J=13, 8 Hz), 3.08 (quintet, 1H, J=7 Hz), 2.64 (s, 3H), 0.84 (s, 9H),-0.05 (s, 3H),-0.06 (s, 3H). Mass spectrum (ESI): m/z=420 (M+1).

1. stirringstirring
2. waitwas continued overnight at room temperature
3. concentrationAfter concentrating in vacuo
4. dissolutionthe residue was dissolved in 50 mL of dichloromethane
5. washwashed with 25 mL of 10% aqueous sodium hydroxide and 25 mL of brine
6. dry with materialThe organic layer was dried over sodium sulfate
7. customdecanted
8. concentrationconcentrated
9. customThe residue was purified by flash column chromatography on silica gel
10. washeluting with 5% ethyl ether in hexane