Diisopropylamine → HCID 18790064, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (7.2 mL, 52 mmol) is dissolved in THF (85 mL), cooled to -78° C. and n-butyl lithium in hexanes (23 mL, 52 mmol) is added slowly. The reaction is allowed to warm to -30° C. over 15 minutes and is then recooled to -78° C. A solution of methyl isobutyrate (6 mL, 52 mmol) in THF (15 mL) is added dropwise over 20 minutes and then stirred an additional 40 minutes. Next solution of 5-phenylpentanal (7 g, 43 mmol) in THF (10 mL) is added dropwise over 10 minutes and the reaction is stirred 1 hour. Acetic acid (3 mL) is added slowly followed by a solution of NH4Cl (20 mL) and the reaction is allowed to warm to room temperature. The reaction is partitioned between ether (200 mL) and water (150 mL). The organic phase is washed with 1 N HCl (2×50 mL), NaHCO3 (50 mL) and brine (50 mL). The solution is dried over MgSO4 and concentrated in vacuo to provide methyl 3-hydroxy-2,2-dimethyl-7-phenylheptanoate (11.2, 99%): 1H NMR (300 MHz, CDCl3) δ 7.30-7.24 (m, 2H), 7.18-7.16 (m, 3H), 3.68 (s, 3H), 3.60 (dd, J=9.7, 1.9 Hz, 1H), 2.61 (t, J=7.5 Hz, 2H), 2.37 (s, 1H), 1.73-1.20 (m, 6H), 1.17 (s, 3H), 1.15 (s, 3H); MS (EI) m/e 264 (M+).

Provenance & Evidence