反応 #66663

反応方程式

5-isopropyl-6-methoxy-2,3-dihydro-benzo[1,4]dioxine

BBr3

→

5-isopropyl-6 hydroxy-2,3-dihydro-benzo[1,4]dioxine

収率 65.4%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   温度After 16 hours the solution was cooled to −78° C.
2. 2
   その他quenched with H2O
3. 3
   温度warmed to room temperature
4. 4
   抽出extracted with CH2Cl2
5. 5
   洗浄The combined organics were washed with brine
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他Purification via flash chromatography (7:3 hexane/ethyl acetate)

実験手順

To a solution of 5-isopropyl-6-methoxy-2,3-dihydro-benzo[1,4]dioxine (1.011 g, 4.9 mmol) in 15 ml CH2Cl2 at −78° C. was added BBr3 (7.3 ml, 7.3 mmol). The solution was allowed to warm to room temperature. After 16 hours the solution was cooled to −78° C., quenched with H2O, warmed to room temperature and extracted with CH2Cl2. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography (7:3 hexane/ethyl acetate) afforded 5-isopropyl-6 hydroxy-2,3-dihydro-benzo[1,4]dioxine (0.622 g, 63%) as a pale yellow oil.

出典