4-Bromoanisole → 3,5-Di-(tert-butyldimethylsilyloxy)-4'-methoxybenzhydrol

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Combining 4-bromoanisole (0.43 g) and aldehyde 9a (0.76 g) provided 3,5-di-(tert-butyldimethylsilyloxy)-4′-methoxybenzhydrol 15d as a faint yellow oil (0.80 g, 82%): EIMS m/z 474 (M+), 459, 417, 361, 343, 73; IR (KBr, cm−1) νmax 3420, 2932, 2859, 2361, 1591, 1451, 1252, 1163, 1026, 833; 1H-NMR δ 7.29 (2H, d, J=9.04 Hz), 6.89 (2H, d, J=9.0 Hz), 6.52 (2H, d, J=2.0 Hz), 6.28 (1H, t, J=2.0 Hz), 5.70 (1H, s), 3.83 (3H, s, OCH3), 1.00 (18H, s, C(CH3)3×2), 0.20 (12H s, Si(CH3)2×2); 13C-NMR (75.5 MHz) δ 159.0, 156.5, 146.1, 136.0, 127.9, 113.7, 111.5, 111.0, 75.5, 55.3, 25.7, 18.2, −4.4. Anal. (C26H42O4Si2) C, H.

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