Reaction #9402

Reaction equation

TBSCl

14

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

Et3N

→

benzo[b]furan

Yield 92.2%

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

Yield 92.2%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Otherallowing too reach room temperature
2. 2
   OtherThe reaction was quenched with water
3. 3
   Otherthe phases separated
4. 4
   Extractionthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
5. 5
   DryingThe combined organic solutions were dried over MgSO4
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherPurification
8. 8
   Washby flash column chromatography (silica gel, elution with hexanes)

Procedure

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.

Source