Pyridine → HCID 59199372, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-chloro-3-hydroxy-2,2-dimethyl-indan-1-one, which can be prepared as described in Example 58, (287 mg, 1.36 mmol) in dichloromethane (15 mL) is added pyridine (1.1 mL, 13.6 mmol), and acetic anhydride (0.26 mL, 2.72 mmol). The reaction is permitted to stir for 1 hour and is then diluted with water and extracted twice with dichloromethane. The combined organic extracts are washed successively with 4N aqueous HCl and saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated. The resulting residue is then diluted with ethanol (10.0 mL) and cooled to −10° C. The solution is then charged with a solution of NaBH4 (100 mg, 2.63 mmol) in ethanol (6 mL). The reaction is permitted to warm to room temperature over 1 hour, at which time additional NaBH4 (50 mg, 1.31 mmol) is added. The reaction is permitted to stir for another 1.5 hours and then diluted with saturated aqueous NH4Cl. The reaction mixture is concentrated to remove the organic volatiles and then extracted three times with ethyl acetate. The organic extracts are combined, dried over Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:2) to furnish acetic acid 4-chloro-3-hydroxy-2,2-dimethyl-indan-1-yl ester; MS: (ESI) m/z 237.17 (M−OH)+

Provenance & Evidence