Diethyl Ether → 1-(1,1-Dimethylethyl)-3-(phenylmethyl)-2-undecylpropanedioate

Participants

Reaction Steps

To a suspension of NaH (160 mg, 4.0 mmol) in DMF (8 mL) at 0° C. under N2, was added benzyl tert-butyl malonate (1.0 g, 4.0 mmol) in DMF (2 mL). The mixture was stirred for 50 min after which 1-bromoundecane in DMF (2 mL) was added. After an additional hour of stirring the reaction was allowed to warm to room temperature. The reaction was maintained overnight. Et2O (100 mL) and water (20 mL) were added to partition the reaction. The aqueous phase was extracted with Et2O (100 mL), and the combined organics dried over Na2SO4. The solvent was evaporated and the residue purified by flash column (C18 12 g, 40-100% ACN/water+0.1% TFA) to yield the title compound as a colorless oil (1.14 g, 2.82 mmol, 71%): LCMS Method F Rt=1.58 min, M+Na 427.4; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.84-0.96 (m, 3H) 1.28 (br. s, 12H) 1.31 (m, J=3.90 Hz, 6H) 1.41 (s, 9H) 1.88 (q, J=7.38 Hz, 2H) 3.29 (t, J=7.58 Hz, 1H) 5.19 (q, J=12.27 Hz, 2H) 7.30-7.42 (m, 5H).

Provenance & Evidence