Iodine → Ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

関与物質

反応手順

A mixture of 6-fluoro-1-indanone (5.0 g, 33.3 mmol), ethyl bromoacetate (8.3 g, 50.0 mmol, Aldrich), activated zinc powder (3.2 g, 50.0 mmol, Mallinckrodt; Org. Synth., Coll. Vol. 6, 290, 1988) and a few crystals of iodine in diethyl ether-benzene (1:1, 100 mL) was heated at reflux under nitrogen for 24 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue in diethyl ether was vigorously stirred with excess dilute ammonium hydroxide, dried and concentrated to give ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate as an amber oil (7.6 g, 97%); NMR (DMSO-d6): d 6.99-7.24 (m, 3H, Ar), 5.38 (s, 1H, OH), 4.00 (q, 2H, CH2CH3), 2.64-2.92 (m, 4H, 2XCH2), 2.45-2.54, 2.05-2.14 (2m's, 2H, CH2CO), 1.08 (t,3H, CH3).

情報源と証拠