Diethyl Malonate → HCID 57222703, compound

Participants

Reaction Steps

A mixture potassium tert-butoxide (1.1 g, 9.6 mmol) and diethyl malonate (3.8 g, 24 mmol) in THF (25 ml) and HMPA (8 ml) was stirred at room temperature under argon atmosphere for 1 hr. To this solution the triflate (8) (1.47 g, 2.4 mmol) in THF (20 ml) was added and the mixture was stirred at room temperature for 26 hr. The usual work-up (ether for extraction) gave a crude product, which was applied to a column of silica gel (100 g). Elution with n-hexane-ether (5:1) provided the diester (9) (1.20 g, 81%), mp 79°-80° C. (ethanol). IR γmaxKBr cm-1 : 1750, 1740. 1H-NMR δ: 0.73 (3H, s, 18-H3), 1.00 (3H, s, 19-H3), 1.10 (3H, d, J=6 Hz, 21-H3), 1.27 (6 H, t, J=7 Hz, --CO2CH2CH3), 3.46 (2H, m, THP), 3.62 (1H, t, J=6 Hz, 25-H), 3.80 (1H,m, 3-H), 4.14 (4H,q,J=JHz, --COCH2CH3), 4.64 (1H,m,THP), 5.30 (1H m, 6-H). MS m/z: 538 (M+ -DHP), 520, 505. Anal. Calcd for C36H56O6F2 : C, 69.40; H, 9.06; F, 6.10. Found: C, 69.19; H, 9.11; F, 5.85.

Provenance & Evidence