6-Bromo-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one → 6-Cyclohexyl-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)2Cl2 (60 mg) in a 40 mL tube under Ar was treated sequentially with 6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (600 mg, 2.01 mmol) in THF (20 mL*3), CuI (600 mg) and cyclohexylzinc(II) bromide (8.1 mL, 4.02 mmol). The mixture was heated under microwave at 160° C. for 10 min. The reaction mixture was concentrated in vacuo to give the residue, which was purified by column chromatography to give 6-cyclohexyl-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (200 mg, 30%). 1H-NMR (CDCl3): 1.31 (t, 4H), 1.48 (m, 1H), 1.62 (m, 5H), 1.76 (d, 4H), 1.89 (m, 1H), 2.06 (d, 1H), 2.49 (s, 1H), 2.61 (m, 2H), 3.49 (m, 2H), 3.79 (m, 2H), 6.88 (d, 1H), 7.29 (d, 2H), 7.61 (s, 1H).

Provenance & Evidence