5-hydroxy-8-methoxy-3,4-dihydro-2H-naphthalen-1-one → HCID 21255658, compound
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=O>FC(F)(F)C(O)=O>[CH3:13][O:12][C:9]1[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:2]([OH:1])=[CH:11][CH:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.), stirred solution of 5-hydroxy-8-methoxy-3,4-dihydro-2H-naphthalen-1-one (1.7 g) in trifluoroacetic acid (20 mL) triethylsilane (4.2 mL) was added and the reaction warmed to RT and then stirred for 1.5 h). The reaction mixture was concentrated in vacuo, partitioned between ethyl acetate/water, the organic layer was washed with water, brine, and then dried over sodium sulfate and concentrated in vacuo. The resulting oil is flash chromatographed (10% ethyl acetate/hexanes) to afford the title compound as a colorless solid (1.6 g).