tert-Butyldimethylsilyl chloride → HCID 68588684, compound

Participants

Reaction Steps

Using procedure analogous to that used to prepare Intermediate 10, Intermediate 9 (7.8 g, 158 mmol) was protected with tert-Butyldimethylchlorosilane to yield (R)-(2-(4-bromo-2-methoxyphenyl)propoxy)(tert-butyl)dimethylsilane (9.2 g, 81% yield) as a clear oil. The protected alcohol (3.00 g, 8.35 mmol) was reacted with BuLi and trimethyl borate to yield Intermediate 10 (1.87 g, 5.77 mmol, 69.1% yield) as a colorless oil. 1H NMR (400 MHz, methanol-d3) 8 ppm 7.12-7.19 (m, 2H) 7.12 (s, 1H) 3.82 (s, 3H) 3.75 (dd, J=9.89, 5.50 Hz, 1H) 3.52-3.58 (m, 0H) 3.32-3.37 (m, 0H) 1.23 (d, J=6.60 Hz, 3H) 0.84 (s, 9H) −0.04 (d, J=2.20 Hz, 6H).

Provenance & Evidence