5-Bromo-1,2,3-trimethoxybenzene → HCID 178418846, compound

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Reaction Steps

To a stirred solution of n-butyllithium (0.5 mL, 1.6 M in hexane solution, 0.80 mmol) in dry ether (20 mL), a solution of 3,4,5-trimethoxyphenylbromide (98.8 mg, 0.40 mmol) in ether (10 mL) was added under dry nitrogen at −78° C. The solution was stirred for 1 h in order to form 3,4,5-trimethoxyphenyllithum. 7-[(tertButyldimethylsilyl)oxy]-6-methoxy-1-tetralone (122 mg, 0.40 mmol) was added at −20° C, and stirring was continued for 2 h (−20° C.-rt). The mixture was partitioned between CH2Cl2 and water, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 7-[(tertbutyldimethylsilyl)oxy]-1-hydroxy-6-methoxy-1-(3′,4′,5′-trimethoxyphenyl)-tetralin (137 mg, 0.29 mmol, 73%) was obtained following purification by column chromatography. 1H-NMR (CDCl3, 300 MHz) 0.04 (s, 6H), 0.89 (s, 9H), 1.80 (b, 1H), 2.11 (m, 4H), 2.81 (t, J=6.5, 2H), 3.79 (s, 6H), 3.81 (s, 3H), 3.84 (s, 3H), 6.49 (s, 1H), 6.56 (s, 2H), 6.59 (s, 1H). 13C-NMR (CDCl3, 75 MHz) −4.3, 18.8, 20.2, 26.1, 29.9, 41.5, 55.8, 56.5, 61.2, 75.6, 104.2, 111.9, 121.2, 131.4, 134.2, 136.8, 143.8, 145.3, 150.9, 152.9.

Provenance & Evidence