Triethylamine → HCID 11168019, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence