تفاعل #9402

معادلة التفاعل

TBSCl

14

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

Et3N

→

benzo[b]furan

المردود 92.2%

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

المردود 92.2%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىallowing too reach room temperature
2. 2
   أخرىThe reaction was quenched with water
3. 3
   أخرىthe phases separated
4. 4
   استخلاصthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
5. 5
   تجفيفThe combined organic solutions were dried over MgSO4
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىPurification
8. 8
   غسيلby flash column chromatography (silica gel, elution with hexanes)

الإجراء التجريبي

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.

المصدر