反応 #9402

反応方程式

TBSCl

14

3-(3′-hydroxy-4′-methoxyphenyl)-6-methoxybenzo[b]furan

Et3N

→

benzo[b]furan

収率 92.2%

3-(3′-tert-Butyldimethylsilyloxy-4′-methoxyphenyl)-6-methoxybenzo[b]furan

収率 92.2%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他allowing too reach room temperature
2. 2
   その他The reaction was quenched with water
3. 3
   その他the phases separated
4. 4
   抽出the aqueous phase was extracted with CH2Cl2 (3×30 mL)
5. 5
   乾燥The combined organic solutions were dried over MgSO4
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他Purification
8. 8
   洗浄by flash column chromatography (silica gel, elution with hexanes)

実験手順

To a solution of 14 (3.51 g, 12.9 mmol) in CH2Cl2 (30 mL), under nitrogen, was added Et3N (1.98 mL, 14.2 mmol) followed by DMAP (0.162 g, 14.2 mmol) and TBSCl (2.4 g, 14.2 mmol) at 0° C. The reaction mixture was stirred for 12 h allowing too reach room temperature. The reaction was quenched with water, the phases separated, and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organic solutions were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, elution with hexanes) afforded 4.57 g (11.9 mmol, 92%) of the protected benzo[b]furan 15 as a colorless oil.

出典