Ethyl acetate hexane → HCID 59271890, compound

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Reaction Steps

A mixture of ethyl (2E)-4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enoate (23 g, 90 mmol) and 5% Pt on carbon (3 g, 14.65 mmol) in ethanol (200 mL) was shaken on the Parr under 45 psi of hydrogen for 5 days (complete conversion by TLC: 10% EtOAc/hexane-no UV active spots). The catalyst was filtered off catalyst and the filtrate concentrated. Drying under vacuum gave ethyl 4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentanoate as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 4.7 (t, 1H), 4.12 (q, 2H), 3.8 (m, 1H), 3.5 (m, 1H), 3.4 (d, 1H), 3.0, (d, 1H), 2.3 (m, 2H), 1.8 (m, 1H), 1.7-1.5 (m, 6H), 1.9 (s, 3H), 1.88 (s, 3H).

Provenance & Evidence