Reaktion #2174203

Reaktionsgleichung

3,4-bis-(t-butyldimethylsilyloxy)-5-chlorophenol

t-butyldimethylsilyl chloride

triethylamine

→

14

Ausbeute 83.0%

1,2,5-tris-(t-Butyldimethylsilyloxy)-3-chlorobenzene

Ausbeute 83.0%

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with diethyl ether (50 mL each)
2. 2
   WaschenThe combined extracts were washed with 30 mL of brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   Sonstigecolumn chromatographed on silica gel using
6. 6
   workup.ADDITIONa gradient mixture of hexane and diethyl ether as eluent

Vorschrift

To a mixture of 1.028 g (2.65 mmol) of 3,4-bis-(t-butyldimethylsilyloxy)-5-chlorophenol, 0.600 g (4.00 mmol) of t-butyldimethylsilyl chloride, and 0.048 g (0.40 mmol) of 4-dimethylaminopyridine in 10 mL of dichloromethane under argon at 25° C. was added 1.30 mL (9.26 mmol) of triethylamine. After stirring at 25° C. for 10 h, the mixture was diluted with 30 mL of water and extracted three times with diethyl ether (50 mL each). The combined extracts were washed with 30 mL of brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a gradient mixture of hexane and diethyl ether as eluent to give 1.100 g (83% yield) of 14. 1H NMR (CDCl3) d 6.49 (d, J=2.8 Hz, 1H, Ar, C4-H), 6.30 (d, J=2.8 Hz, 1H, C6-H), 1.04˜0.97 (broad s, 27H, t-Bu), 0.18 (s, 6H, Me), 0.175 (s, 12H, Me); 13C NMR (CDCl3) d 149.3 (s), 148.6 (s), 138.6 (s), 126.8 (s), 114.6 (d), 112.1 (d), 26.3 (q, t-Bu), 25.9 (q, t-Bu), 18.9 (s), 8.8 (s), −3.5 (q, 2C, Me), −3.4 (q, 2C, Me), −4.3 (q, 2C, Me). Anal. Calcd for C24H47ClO3Si3: C, 57.27; H, 9.41. Found: C, 57.37; H, 9.55.

Quelle