Hydride → (R)-6-Bromo-11-[3,5-dibromo-4-(1-hydroxymethyl-2-phenyl-ethoxy)-phenyl]-benzo[b]naphtho[2,3-d]thiophene

Beteiligte Stoffe

Reaktionsschritte

A solution of R)-2-[2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11 -yl)-phenoxy]-3-phenyl-propionic acid, methyl ester (0.30 g, 0.414 mmol) in THF (4.2 mL) was added dropwise to a -78 ° C., stirred solution of mixed hydride (0.435 mL, 0.414 mmol) of lithium aluminum hydride/aluminum chloride (1.0 M solution in THF) in THF (3 mL) under a dry nitrogen atmosphere over a period of 5 min. After 1 h., the solution was allowed to warm to ambient temperature. After 2 h. the reaction mixture was quenched carefully with methanol (3 mL) and further diluted with water (80 mL). Aqueous mixture was extracted with ethyl acetate (2×80 mL). The ethyl acetate extracts were washed with water, dried with brine and anhydrous MgSO4, and concentrated to provide the title compound as a white solid (0.28 g, 97%): mp 83-85: MS (EI): [M+], 3 bromine isotope pattern, 694, 696, 698, 700.

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