Tetrahydrofuran → HCID 22504114, compound
Reaction equation
CON(C)[C:4](=[O:17])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH3:16].[CH2:19]1COCC1>O>[CH3:16][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[CH2:5][C:4](=[O:17])[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-methoxy-N-methyl-2-(2-methyl-naphthalen-1-yl)-acetamide (1.01 g, 4.16 mmol) was dissolved in freshly distilled THF (17 mL) in an argon-purged, round-bottom flask. The mixture was chilled to 0° C. and methyl magnesium bromide (2.08 mL of 3.0 M soln in Et2O, 6.23 mmol) was added via syringe. The reaction was stirred at 0° C. for 75 minutes. TLC analysis (silica, 20% acetone-hexanes) indicated complete consumption of the starting material. The reaction was carefully quenched with a mixture of AcOH (1 mL) in EtOAc (5 mL). The quenched reaction was diluted with H2O and extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. Purification by flash chromatography (SiO2, 20% EtOAc-hexane) gave 1-(2-methyl-naphthalen-1-yl)-propan-2-one (343 mg, 1.73 mmol) in 41% yield. MS (APCI) m/z 199.1 (M+H). 1H NMR (300 MHz) CDCl3 δ 7.85 (m, 2H), 7.72 (d, J=9.4 Hz, 1H), 7.47 (m, 2H), 7.36 (d, J=8.2 Hz, 1H), 4.18 (s, 2H), 2.51 (s, 3H), 2.10 (s, 3H).