inden-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of epoxy indenol 6 (0.24 g, 1.42 mmol) in 40 mL of CH2 Cl2, were added 2.16 g of oven dried Celite and PDC (2.16 g, 4 eq) at rt. After stirring at rt for 18 hr, the mixture was passed through 2 cm of flash silica gel pad, washed with 5% MeOH in CH2Cl2 (50 mL). The filtrate was concentrated and chromatographed with 35% EtOAc in hexane to give 0.18 g (75%) of indene-1-one 7 as colorless oil. The compound was identical with the literature by NMR (A. R. Daniewski; J. Kiegoel, J. Org. Chem. 1988, 53, 5534-5535). washed with 5% MeOH in CH2Cl2 (50 mL) The filtrate was concentrated chromatographed with 35% EtOAc in hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The indenone of formula 23 prepared in Step 2 is dissolved in CH2Cl2, 1M Br2 solution (dissolved in CH2Cl2) is added thereto. The resulting mixture is stirred for 2 to 3 h at room temperature, to obtain the 2-bromoindenone of formula 17.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The indenone compound prepared in Step 5 is mixed with HBr/AcOH (1:2), and then the resulting mixture is allowed to reflux for 14 to 16 h with stirring, to obtain the 5-hydroxyindenone of formula 19. to reflux for 14 to 16 h

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The indenone compound of formula 16 prepared in Step 3 is dissolved in CCl4, N-bromosuccinimide (1 to 1.2 eq) and 2,2′-azobisisobutyronitrile (10 to 15 wt %) are added thereto. The resulting mixture is allowed to reflux for 2 to 3 h with stirring, to obtain the 2-bromoindenone of formula 17. to reflux for 2 to 3 h

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Bromoindan-1-one (1.5) was dissolved in diethyl ether (10 ml). The temperature was kept at +2-+4 while TEA (2.7 ml) was added. The resulting mixture was further stirred at +2-+4 for 2 hours. The precipitated salt was filtered off and the filtrate evaporated. The crude inden-1-one was used for further reaction without purification. Yield was 0.9 g. was added The precipitated salt was filtered off the filtrate evaporated The crude inden-1-one was used for further reaction without purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Bromoindan-1-one (1.5) was dissolved in diethyl ether (10 ml). The temperature was kept at +2-+4 while TEA (2.7 ml) was added. The resulting mixture was further stirred at +2-+4 for 2 hours. The precipitated salt was filtered off and the filtrate evaporated. The crude inden-1-one was used for further reaction without purification. Yield was 0.9 g. was added The precipitated salt was filtered off the filtrate evaporated The crude inden-1-one was used for further reaction without purification