Reaktion #9402

Reaktionsgleichung

TBSCl

14

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

Et3N

→

benzo[b]furan

Ausbeute 92.2%

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

Ausbeute 92.2%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeallowing too reach room temperature
2. 2
   SonstigeThe reaction was quenched with water
3. 3
   Sonstigethe phases separated
4. 4
   Extraktionthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
5. 5
   TrocknenThe combined organic solutions were dried over MgSO4
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigePurification
8. 8
   Waschenby flash column chromatography (silica gel, elution with hexanes)

Vorschrift

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.

Quelle