Hydrochloric Acid → HCID 10615819, compound

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Reaction Steps

Compound D (4.09 g, 13.46 mmol) was dissolved in 7 mL of freshly distilled THF. Argon was passed through the mixture for 20 min. The solution was cooled in an ice-water bath. BH3—THF solution (1.0 M, 5.05 mL, 5.05 mmol) was added dropwise with stirring. After the addition, the mixture was stirred at 0° C. for 2 h. Water (about 1 mL) was added dropwise to destroy the excess borane until hydrogen evolution ceased. NaOH solution (2 N, 3.4 mL) and 30% H2O2 solution (1.7 mL, 16.2 mmol) were added. The mixture was stirred for 30 min and neutralized with 5% HCl solution. The organic compounds were extracted with EtOAc (3×50 mL), washed with water (3×30 mL), and dried over MgSO4. The solvent was evaporated, and the residue was purified on a silica gel column (EtOAc/hexanes=1/3, v/v) to give 3.19 g (70%) of the product. 1H NMR (CDCl3) δ4.91 (s, 2H), 3.63 (s, 3H), 3.60 (t, J=6.0 Hz, 2H), 2.81 (t, J=7.4 Hz, 2H), 2.56 (s, 2H), 2.38 (s, 3H), 2.24 (s, 3H), 1.77 (m, 2H), 1.45 (s, 6H).

Provenance & Evidence