Oxalyl chloride → 6-(Methyloxy)-3-(3,3,3-trifluoropropyl)-3,4-dihydro-1(2H)-naphthalenone

Participants

Reaction Steps

6,6,6-Trifluoro-3-{[3-(methyloxy)phenyl]methyl}hexanoic acid (120) (1.56 g, 5.38 mmol) was treated with oxalyl chloride followed by AlCl3 in CH2Cl to give 1.07 g (73%) of the title compound (121) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.65-1.75 (m, 2H), 2.10-2.35 (m, 4H), 2.65-2.80 (m, 2H), 2.90-3.05 (m, 1H), 3.85 (s, 3H), 6.70 (d, J=2.4 Hz, 1H), 6.84 (dd, J1=8.8 Hz, J2=2.5 Hz, 1H), 7.99 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 273 (M+H)+.

Provenance & Evidence