Diethyl Ether → HCID 58288630, compound

Participants

Reaction Steps

Acrylic acid chloride (996 mg, 11 mmol) was added dropwise within 5 min to a stirred suspension of the bis-methoxyamine 3 (881 mg, 5 mmol), Na2CO3 (2.65 g, 25 mmol) and BHT (=2,6-tert-butyl-4-methylphenol) (10 mg) in anhydrous diethylether (100 ml) accompanied by ice-cooling. The reaction mixture was then left to heat up to room temperature and stirred for a further 16 h. After the bis-methoxyamine 3 was completely consumed, water (20 ml) was added, the organic phase separated off and the aqueous phase extracted with diethyl ether (3×20 ml). The organic phases were combined, the solvent removed under vacuum and the crude product purified using column chromatography (silica gel, eluent chloroform/ethyl acetate 3:1). 1.1 g (79%) 1,6-bis(N-acryloyl-N-methoxyamino)hexane 4 was obtained. 1H-NMR (300 MHz, CDCl3): δ=1.31-1.36 (m, 4H), 1.59-1.69 (m, 4H), 3.65 (t, J=7.2 Hz, 4H), 3.68 (s, 6H), 5.74 (dd, J=10.3, 2.1 Hz, 2H), 6.41 (dd, J=17.1, 2.1 Hz, 2H), 6.71 (dd, J=17.1, 10.3 Hz, 2H) ppm. 13C-NMR (75 MHz, CDCl3): δ=26.4 (2 CH2), 26.9 (2 CH2), 44.9 (2 CH2), 62.1 (2 CH3), 126.2 (CH), 128.9 (CH2), 166.1 (2 C) ppm.

Provenance & Evidence