반응 #168984

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

BBr3

→

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

수율 65.4%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도After 16 hours the solution was cooled to −78° C.
2. 2
   기타quenched with H2O
3. 3
   온도warmed to room temperature
4. 4
   추출extracted with CH2Cl2
5. 5
   세척The combined organics were washed with brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타Purification via flash chromatography (7:3 hexane/ethyl acetate)

실험 절차

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.

출처