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

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3,3,2-Trimethyl-1-indanone (9.03 g, 50 mmol) as prepared above was dissolved in THF (40 ml) and added to the suspension of LiAlH4 (3.80 g, 100 mmol, 2 equiv.) in THF (10 ml). The mixture was heated to reflux for 2 h, then cooled to 5° C. and hydrolysed via addition of 2N aq. HCl-solution. The crude product obtained after extraction with MTBE, washing with sat. aq. NaHCO3 solution and brine, drying over MgSO4 and concentrating in a rotary evaporator was distilled at 0.1 mbar/72-73° C. to yield 8.70 g (95%) of product as a colourless viscous oil. The compound was obtained as a mixture of diastereomers 87:13, the major isomer being the 1,2-trans compound upon NMR-analysis. The mixture was heated to reflux for 2 h The crude product obtained after extraction with MTBE washing with sat. aq. NaHCO3 solution and brine drying over MgSO4 concentrating in a rotary evaporator was distilled at 0.1 mbar/72-73° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3,3,2-Trimethyl-1-indanone (9.03 g, 50 mmol) as prepared above was dissolved in THF (40 ml) and added to the suspension of LiAlH4 (3.80 g, 100 mmol, 2 equiv.) in THF (10 ml). The mixture was heated to reflux for 2 h, then cooled to 5° C. and hydrolysed via addition of 2N aq. HCl-solution. The crude product obtained after extraction with MTBE, washing with sat. aq. NaHCO3 solution and brine, drying over MgSO4 and concentrating in a rotary evaporator was distilled at 0.1 mbar/72-73° C. to yield 8.70 g (95%) of product as a colourless viscous oil. The compound was obtained as a mixture of diastereomers 87:13, the major isomer being the 1,2-trans compound upon NMR-analysis. The mixture was heated to reflux for 2 h The crude product obtained after extraction with MTBE washing with sat. aq. NaHCO3 solution and brine drying over MgSO4 concentrating in a rotary evaporator was distilled at 0.1 mbar/72-73° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: KH (32 g at 35% in mineral oil, 280 mmol, 1.4 equiv.) was suspended in THF (160 ml) and 3,3-dimethyl-1-indanone (as prepared as described above, 32 g, 200 mmol) in THF (150 mmol) was added. The green suspension was stirred for 1.5 h at RT, then triethylborane (1M solution in THF, 280 ml, 280 mmol, 1.4 equiv.) was added slowly. After 1 h stirring at RT methyl iodide (40 g, 280 mmol, 1.4 equiv.) was added and the suspension stirred for 48 h at RT. Treatment with H2O (240 ml), 10% aq. NaOH (240 ml) and 30% aq. H2O2-solution (240 ml) under occasional cooling was followed by extraction with MTBE. The organic layer was washed with brine, dried over MgSO4 and concentrated in a rotary evaporator. Bulb-to-bulb distillation (0.05 mbar/100° C.) yielded 24.8 g (71%) of product. was added the suspension stirred for 48 h at RT was followed by extraction with MTBE The organic layer was washed with brine dried over MgSO4 concentrated in a rotary evaporator distillation (0.05 mbar/100° C.)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: KH (32 g at 35% in mineral oil, 280 mmol, 1.4 equiv.) was suspended in THF (160 ml) and 3,3-dimethyl-1-indanone (as prepared as described above, 32 g, 200 mmol) in THF (150 mmol) was added. The green suspension was stirred for 1.5 h at RT, then triethylborane (1M solution in THF, 280 ml, 280 mmol, 1.4 equiv.) was added slowly. After 1 h stirring at RT methyl iodide (40 g, 280 mmol, 1.4 equiv.) was added and the suspension stirred for 48 h at RT. Treatment with H2O (240 ml), 10% aq. NaOH (240 ml) and 30% aq. H2O2-solution (240 ml) under occasional cooling was followed by extraction with MTBE. The organic layer was washed with brine, dried over MgSO4 and concentrated in a rotary evaporator. Bulb-to-bulb distillation (0.05 mbar/100° C.) yielded 24.8 g (71%) of product. was added the suspension stirred for 48 h at RT was followed by extraction with MTBE The organic layer was washed with brine dried over MgSO4 concentrated in a rotary evaporator distillation (0.05 mbar/100° C.)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3,3,2-Trimethyl-1-indanone (9.03 g, 50 mmol) as prepared above was dissolved in THF (40 ml) and added to the suspension of LiAlH4 (3.80 g, 100 mmol, 2 equiv.) in THF (10 ml). The mixture was heated to reflux for 2 h, then cooled to 5° C. and hydrolysed via addition of 2N aq. HCl-solution. The crude product obtained after extraction with MTBE, washing with sat. aq. NaHCO3 solution and brine, drying over MgSO4 and concentrating in a rotary evaporator was distilled at 0.1 mbar/72-73° C. to yield 8.70 g (95%) of product as a colourless viscous oil. The compound was obtained as a mixture of diastereomers 87:13, the major isomer being the 1,2-trans compound upon NMR-analysis. The mixture was heated to reflux for 2 h The crude product obtained after extraction with MTBE washing with sat. aq. NaHCO3 solution and brine drying over MgSO4 concentrating in a rotary evaporator was distilled at 0.1 mbar/72-73° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: KH (32 g at 35% in mineral oil, 280 mmol, 1.4 equiv.) was suspended in THF (160 ml) and 3,3-dimethyl-1-indanone (as prepared as described above, 32 g, 200 mmol) in THF (150 mmol) was added. The green suspension was stirred for 1.5 h at RT, then triethylborane (1M solution in THF, 280 ml, 280 mmol, 1.4 equiv.) was added slowly. After 1 h stirring at RT methyl iodide (40 g, 280 mmol, 1.4 equiv.) was added and the suspension stirred for 48 h at RT. Treatment with H2O (240 ml), 10% aq. NaOH (240 ml) and 30% aq. H2O2-solution (240 ml) under occasional cooling was followed by extraction with MTBE. The organic layer was washed with brine, dried over MgSO4 and concentrated in a rotary evaporator. Bulb-to-bulb distillation (0.05 mbar/100° C.) yielded 24.8 g (71%) of product. was added the suspension stirred for 48 h at RT was followed by extraction with MTBE The organic layer was washed with brine dried over MgSO4 concentrated in a rotary evaporator distillation (0.05 mbar/100° C.)