Dimethylformamide dimethyl acetal → 1-(Adamantan-1-yl)-3-(dimethylamino)prop-2-en-1-one

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Reaction Steps

A solution of 17.83 g (0.10 mol) of 1-adamantyl methyl ketone in 35.75 g (0.30 mol) of dimethylformamide dimethylacetal was heated at reflux for 24 hours. After cooling and removal of the solvent in vacuo at 45° to 50° C., the residue was purified by silical gel chromatography to yield 8.64 g (37%) of a white solid: Rf 0.20 in 50% EtOAc/Ligroin; 1H NMR (CDCl3) δ 1.68 (S, 6H, the δ hydrogens of the adamantyl ring, methylene protons at the farthest position from the substituent), 1.81 (S, 6H, the β hydrogens of the adamantyl ring, methylene protons at the closest position to the substituent), 2.00 (S, 3H, the three bridgehead protons, 2.90 (br S, 6H, N(CH3)2), 5.20 (d, 1H, J=14 Hz, O=C-CH), 7.60 (d 1H, J=14 Hz, =C-N<). All analytical data confirmed the assigned structure.

Provenance & Evidence