反応 #79579
ord-74c8f6b4c9fc4a698743832bc6f1b3db
反応方程式
反応条件
後処理
- 1温度The solution was cooled in an ice-bath
- 2workup.STIRRINGthe mixture was stirred at room temperature for 18 hours
- 3濃縮The reaction mixture was concentrated under reduced pressure
- 4その他the residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (150 ml, 0.5N)
- 5その他The layers were separated
- 6抽出extracted with further dichloromethane (3×30 ml)
- 7乾燥The combined organic solutions were dried (MgSO4)
- 8その他evaporated under reduced pressure
- 9その他The residue was purified by chromatography on silica gel (gradient elution 98:2:0.2 to 97:3:0.3 dichloromethane:methanol:0.88 NH3)
実験手順
A solution of (R)-(−)-1-amino-2-propanol (9.00 g, 0.12 mol) in tetrahydrofuran (40 ml) and acetic acid (5 ml) was added dropwise to a solution of p-anisaldehyde (5.45 g, 0.04 mol) in tetrahydrofuran (40 ml), and once addition was complete, the solution was stirred at room temperature for 2 hours. The solution was cooled in an ice-bath, and sodium triacetoxyborohydride (9.50 g, 0.0.045 mol) was added portionwise, and then the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (150 ml, 0.5N). The layers were separated and the aqueous phase was saturated with sodium chloride, then extracted with further dichloromethane (3×30 ml). The combined organic solutions were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (gradient elution 98:2:0.2 to 97:3:0.3 dichloromethane:methanol:0.88 NH3) to afford an orange oil (4.9 g). 1H-NMR (CDCl3, 400 MHz) δ: 1.12 (d, 3H), 2.39 (dd, 1H), 2.70 (dd, 1H), 3.62-3.79 (m, 6H), 6.82 (d, 2H), 7.19 (d, 2H). LRMS: m/z (ES+) 196 [MH+].