Chlorotrimethylsilane → HCID 58292869, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Zn (2.91 g, 44.5 mmol) in THF (10 mL) was added TMSCl (0.833 ml, 6.57 mmol) at 40° C. The temperature was increased to 55° C. over 30 min. Then, the temperature was lowered to 37° C. and bromo ethyl acetate (4.55 mL, 41.1 mmol) was added slowly. The resulting solution was stirred for 30 min from 45° C. to room temperature and stood by for 1 h. The top clear layer (3 mL) was added to a solution of 2-benzyloxy-4-(tetrahydro-pyran-2-yloxy)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (1.50 g, 3.42 mmol) in THF (5 ml) at −78° C. After the addition, the reaction was warmed to 0° C. using an ice bath and stirred at 0° C. 30 min. The reaction mixture was quenched with NH4Cl and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=3:2) to afford the title compound (1.06 g, 73%). MS calcd for (C23H27BO7+H)+: 427.2. MS found: (M+H)+=427.2.

Provenance & Evidence