Ethyl Acetate → HCID 9874234, compound

Participants

Reaction Steps

To a stirred solution of 1.36 g (2.12 mole) of the product of Example 104 in 20 mL tetrahydrofuran at -78° C. was added dropwise 4.7 mL (4.66 mL) 1.0M LiB(C2H5)3H in THF (Super-Hydride [trademark]). The mixture was allowed to come to room temperature over 3 hours, then quenched with 10 mL 10% ammonium chloride. The mixture was poured into water, acidified to ph 1-4 with 1N HCl and then extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 30% ethyl acetate in hexanes gave 670 mg (48%) of pure product. NMR (CDCl3): δ1.40 (s, 3H); 1.53 (s, 3H); 2.10 (m, 1H); 2.90 (m, 2H); 3.88 (s, 3H); 4.23 (s, br, 1H); 5.29 (s, 2H). MS (LSIMS) m/e: 644 (M+, 12), 627 (32), 268 (100).

Provenance & Evidence