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Reference Example 9 5-Fluoro-6-methoxy-1-indanone In the same manner as in Reference Example 6, the target compound was obtained from 3-(3-fluoro-4-methoxyphenyl)propionic acid. The yield was 91percent. m.p.: 152-153° C. (recrystallized from methanol/ethyl acetate); NMR (CDCl3) delta: 2.71 (2H, t, J=5.7 Hz), 3.08 (2H, t, J=5.7 Hz), 3.92 (3H, s), 7.17 (1H, d, J=10.3 Hz), 7.29 (d, J=8.1 Hz); Elemental Analysis for C10 H9 FO2: Calcd.: C 66.66; H 5.03; Found: C 66.82; H 5.06
A mixture of Compound II (900 mg), toluene (9 mL) and thionyl chloride (393 muL) was stirred at 90° C. for one hour, and concentrated under reduced pressure. The obtained residue was added to an ice-cold solution of aluminium chloride (605 mg) in methylene chloride (45 mL), and the mixture was stirred for one hour. The reaction solution was added dropwise into ice-cold water, and the mixture was stirred for one hour, ane extracted with ether. The organic layer was washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to give Compound III (666 mg).
Reference Example 23 5-Fluoro-6-methoxy-1-indanone Starting with 3-(3-fluoro-4-methoxyphenyl)propionic acid, the title compound was synthesised in otherwise the same manner as Reference Example 11 (yield 94percent). m.p. 152-154° C. NMR(CDCl3) delta: 2.70(2H,t,J=5.5 Hz), 3.07(2H,t,J=5.5 Hz), 3.91(3H,s), 7.17(1H,d,J=10.3 Hz), 7.29(1H,d,J=10.3 Hz). Elemental analysis for C10 H9 FO2: Calcd.: C, 66.66; H, 5.03. Found: C, 66.85; H, 4.97.
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