Propanal → 2-(2-Oxobutyl)-4-hydroxy-1-indanone

Participants

Reaction Conditions

Reaction Steps

6-Hydroxy-2-methylene-1-indanone was prepared using a similar method to that described in Example 16 but using 6-hydroxy-1-indanone instead of 4-hydroxy-1-indanone. To the above compound (0.3 g; 1.87 mmol) in suspension in ethanol, were added, at ambient temperature, under argon: propionaldehyde (0.27 ml; 3.75 mmol), triethylamine (80 μl; 0.56 mmol) and 3,4-dimethyl-5-(2hydroxyethyl)thiazolium iodide (50.6 mg; 0.18 mmol). The mixture was heated at 80° C. for 17 hours. The solution was taken up in CH2Cl2 and washed in water and a saturated solution of NaCl. The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (7/3), to give 2-(2-oxobutyl)-4-hydroxy-1-indanone (0.28 g; 70%).

Provenance & Evidence