Methanol → HCID 14059378, compound

Participants

Reaction Steps

To a solution of ethyl 4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanoate (11.3 g, 43.7 mmol) in toluene (300 mL) cooled to −78° C. under nitrogen was added diisobutylaluminum hydride 1.0M in heptane (53 mL, 52.5 mmol) slowly, keeping the internal temperature below −70° C. The mixture was allowed to stir in the cold for 15 minutes (TLC: 20% EtOAc in hexane). The reaction was quenched with MeOH (3.00 mL, 161 mmol) allowed to warm to −10 C, diluted with 500 mL of ethyl acetate and 500 mL of saturated NaCl. The mixture was allowed to warm and stir for 60 minutes forming a gel. The gelatinous mixture was filtered through diatomaceous earth and washed with 750 mL of ethyl acetate. The organic layer was separated, dried over MgSO4 and concentrated. Drying under vacuum gave 4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanal as a clear oil: 1H NMR (400 MHz, CDCl3) δ 9.8 (s, 1H), 4.6 (t, 1H), 3.8 (m, 1H), 3.6 (m, 1H), 3.5 (d, 1H), 3.0, (d, 1H), 2.4 (m, 2H), 1.8 (m, 1H), 1.7-1.5 (m, 6H), 0.93 (s, 3H), 0.92 (s, 3H).

Provenance & Evidence