Reaktion #2174202

Reaktionsgleichung

13

3,4-bis(t-Butyldimethylsilyloxy)-5-chlorobenzaldehyde

m-chloroperbenzoic acid

→

3,4-bis-(t-butyldimethylsilyloxy)-5-chlorophenyl formate

Ausbeute 70.0%

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter refluxing for 10 h
2. 2
   Extraktionextracted three times with diethyl ether (50 mL each)
3. 3
   WaschenThe combined extracts were washed twice with saturated aqueous NaHCO3 (30 mL each), 30 mL of water, and 30 mL of brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated
6. 6
   Sonstigecolumn chromatographed on silica gel

Vorschrift

To a solution of 1.73 g (4.30 mmol) of 13 in 15 mL of dichloromethane under argon was added 2.03 g (6.50 mmol) of 55% m-chloroperbenzoic acid (MCPBA). After refluxing for 10 h, the solution was diluted with 30 mL of water and extracted three times with diethyl ether (50 mL each). The combined extracts were washed twice with saturated aqueous NaHCO3 (30 mL each), 30 mL of water, and 30 mL of brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using hexane as eluent to give 1.24 g (70% yield) of 3,4-bis-(t-butyldimethylsilyloxy)-5-chlorophenyl formate. 1H NMR (CDCl3) δ 8.22 (s, 1H, CHO), 6.79 (d,J=3.2 Hz, 1H), 6.58 (d,J=3.2 Hz, 1H), 1.03 (s, 9H, t-Bu), 0.96 (s, 9H, t-Bu), 0.22 (s, 6H, Me), 0.19 (s, 6H, Me); 13C NMR (CDCl3) δ 159.0 (s, C═O), 148.8 (s), 143.0 (s), 142.4 (s), 127.1 (s), 115.5 (d), 113.1 (d), 26.2 (q, 6C, t-Bu), 18.8 (s, 2C, t-Bu), −3.3 (q, 2C, Me), −3.6 (q, 2C, Me).

Quelle