2,2-dimethyl-3H-inden-1-one

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

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

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diethylamine (8.76 g, 0.12 mol) was cooled to 0° C. and 62.5% aq. H2SO4 was added slowly. Aqueous formaldehyde solution (36.5%, 9.86 g, 0.12 mol) was added, followed by dimethylindanone (16.0 g, 0.10 mol). The mixture was heated to 110° C. for 5.5 h. Aqueous workup yielded a ca. 1:1 mixture of starting material and product which was separated by FC on SiO2 to yield the product as a colourless oil (2.73 g, 13%). Aqueous workup yielded a ca. 1:1 mixture of starting material and product which was separated by FC on SiO2

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

Procedure: Ethylformate (8.10 g, 110 mmol) in THF (50 ml) was added to the suspension of NaH (55% in mineral oil, 4.80 g, 110 mmol) in THF (50 ml). After stirring for 5 min at RT Dimethylindanone (16.0 g, 100 mmol)in THF (50 ml) was added. Gas evolution started and the temperature of the mixture rose and was controlled with an icebath to not exceed 40° C. After further stirring for 4.5 h at RT, methyl iodide (42.6 g, 300 mmol) was added und stirring continued for 48 h. After quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%) of was obtained. was added exceed 40° C und stirring continued for 48 h After quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%) of was obtained

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

Procedure: Ethylformate (8.10 g, 110 mmol) in THF (50 ml) was added to the suspension of NaH (55% in mineral oil, 4.80 g, 110 mmol) in THF (50 ml). After stirring for 5 min at RT Dimethylindanone (16.0 g, 100 mmol)in THF (50 ml) was added. Gas evolution started and the temperature of the mixture rose and was controlled with an icebath to not exceed 40° C. After further stirring for 4.5 h at RT, methyl iodide (42.6 g, 300 mmol) was added und stirring continued for 48 h. After quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%) of was obtained. was added exceed 40° C und stirring continued for 48 h After quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%) of was obtained

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

Procedure: To a solution of 2,2-dimethyl-indan-1-one, which can be prepared as described in Ranu, B. C.; Jana, U. Journal of Organic Chemistry, 1999, 64, 6380-6386, (13.0 g, 81.3 mmol) in methanol (200 mL) at −20° C. is added NaBH4 (3.07 g, 81.3 mmol). Upon complete consumption of the starting ketone, as determined by TLC analysis, the reaction is quenched with saturated aqueous NH4Cl. The reaction mixture is then concentrated to near dryness, diluted with ethyl acetate and washed with water. The organic layer is then dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:8) to provide 2,2-dimethyl-indan-1-ol. 1H NMR (400 MHz, CDCl3) δ ppm 1δ ppm 1.05 (s, 3 H), 1.20 (s, 3 H), 2.56-2.89 (m, 2 H), 4.70 (s, 1 H), 7.16-7.26 (m, 3 H), 7.35-7.42 (m, 1 H). Upon complete consumption of the starting ketone the reaction is quenched with saturated aqueous NH4Cl The reaction mixture is then concentrated diluted with ethyl acetate washed with water The organic layer is then dried with Na2SO4 filtered concentrated The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:8)

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diethylamine (8.76 g, 0.12 mol) was cooled to 0° C. and 62.5% aq. H2SO4 was added slowly. Aqueous formaldehyde solution (36.5%, 9.86 g, 0.12 mol) was added, followed by dimethylindanone (16.0 g, 0.10 mol). The mixture was heated to 110° C. for 5.5 h. Aqueous workup yielded a ca. 1:1 mixture of starting material and product which was separated by FC on SiO2 to yield the product as a colourless oil (2.73 g, 13%). Aqueous workup yielded a ca. 1:1 mixture of starting material and product which was separated by FC on SiO2

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

Procedure: Ethylformate (8.10 g, 110 mmol) in THF (50 ml) was added to the suspension of NaH (55% in mineral oil, 4.80 g, 110 mmol) in THF (50 ml). After stirring for 5 min at RT Dimethylindanone (16.0 g, 100 mmol)in THF (50 ml) was added. Gas evolution started and the temperature of the mixture rose and was controlled with an icebath to not exceed 40° C. After further stirring for 4.5 h at RT, methyl iodide (42.6 g, 300 mmol) was added und stirring continued for 48 h. After quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%) of was obtained. was added exceed 40° C und stirring continued for 48 h After quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%) of was obtained