5-Chlorovaleryl chloride → HCID 86612800, compound

Participants

Reaction Steps

A solution of [3,3-bis(ethyloxy)propyl]amine (9.02 g, 61 mmol) and diisopropylethylamine (13.3 mL, 76.4 mmol) in CH2Cl2 (50 mL) was added dropwise to a cooled (0° C.) solution of 5-chloropentanoyl chloride (10.35 g, 61 mmol) in CH2Cl2 (50 mL) over 2 h. After addition was complete the mixture was treated with 1N NaHSO4 (75 mL) and separated the layers in a separatory funnel. Back extracted the aqueous with CH2Cl2 then combined the organics, washed them with brine, dried them over MgSO4, filtered, and concentrated in vacuo. The resulting oil was chromatographed on silica gel using a gradient between 50 and 100% EtOAC in Hexanes over 100 min. Collected, combined, and concentrated in vacuo pure fractions to provide the desired product as a yellow viscous oil: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.09 Hz, 6 H), 1.44-1.55 (m, 2 H), 1.59-1.75 (m, 4 H), 2.04 (t, J=7.23 Hz, 2 H), 3.01-3.08 (m, 2 H), 3.41 (dq, J=9.55, 7.07 Hz, 2 H), 3.50-3.64 (m, 4 H), 4.48 (t, J=5.69 Hz, 1 H), 7.74 (t, J=4.98 Hz, 1 H); ES+ MS: 288 (M+Na+).

Provenance & Evidence