Ethyl Acetate → HCID 63630296, compound

Participants

Reaction Steps

A solution of N-[3,3-bis(ethyloxy)propyl]-5-chloropentanamide (10 g, 38 mmol) in THF (400 mL) was treated with lithium hexamethyl disilazide (LiHMDS, 1.0 M in THF) (40 mL, 40 mmol) at ambient temperature. After stirring for 15 min., an additional 10 mL of LiHMDS was added and the reaction was stirred an additional 30 min. After TLC (EtOAc) showed the absence of starting material, the reaction was poured into a sep. funnel containing EtOAc (500 mL) and 1N NaHSO4 (500 mL). Back extracted the aqueous with EtOAc then combined the organics, washed them with brine, dried over MgSO4, filtered, and concentrated in vacuo to provide the product as a clear viscous oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.02 Hz, 6 H), 1.63-1.74 (m, 6 H), 2.17 (t, J=6.11 Hz, 2 H), 3.20-3.28 (m, 4 H), 3.42 (dq, J=9.55, 7.07 Hz, 2 H), 3.56 (dq, J=9.55, 7.07 Hz, 2 H), 4.47 (t, J=5.62 Hz, 1 H).

Provenance & Evidence