6-Hydroxy-1-indanone

Chemical Properties

white to light yellow crystal powder

Uses

6-Hydroxy-1-indanone can be used in the synthesis of tetracyclic ketones intermediates during the total syntheses of (±)-frondosin C and (±)-8-epi-frondosin C. It can also be used in the synthesis of 1,4-dihydroindeno[1,2-c]pyrazoles, which can act like potent CHK-1 inhibitors, thereby inhibiting the growth of cancer cells.

Synthesis

6-Methoxy-1-indanone (2.5 g, 15.4 mmol) was slowly added to a stirred suspension of aluminum chloride (5.3 g, 39.7 mmol) in toluene (75 mL) at room temperature and under nitrogen protection. The 6-methoxy-1-indanone remaining in the powder addition funnel was flushed into the reaction mixture using toluene (25 mL). The reaction mixture was heated to reflux and maintained for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water. The mixture was transferred to a dispensing funnel using ethyl acetate. The organic and aqueous layers were separated and the organic phase was sequentially washed twice with water and once with saturated sodium chloride solution, followed by drying with anhydrous magnesium sulfate. The dried organic phase was filtered and the filtrate was concentrated to give 1.5 g (66% yield) of 6-hydroxy-2,3-dihydro-1H-inden-1-one, the product was a light tan solid.1H NMR (400 MHz, DMSO-d6) δ: 9.72 (s, 1H), 7.36 (d, J = 8 Hz, 1H), 7.07 (dd, J = 8, 3 Hz, 1H) , 6.90 (d, J = 3 Hz, 1H), 2.94 (m, 2H), 2.58 (m, 2H).ESI-MS m/z: 149 ([M + H]+).

References

[1] Organic Preparations and Procedures International, 2009, vol. 41, # 4, p. 309 - 314
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 7, p. 1068 - 1083
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 20, p. 5665 - 5670
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1675 - 1678
[5] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292