2-ethylbenzaldehyde

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: The title compound was prepared from 2-ethylbenzaldehyde, 3-aminopyrazole and ethyl 3-ketohexanoate in the same manner as in Example 25.

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

Procedure: The title compound was prepared from 2-ethylbenzaldehyde, 3-aminopyrazole and ethyl 3-ketohexanoate in the same manner as in Example 25.

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

Procedure: Dissolve 2-ethyl benzaldehyde (7 mL, 53.2 mmol), nitromethane (8.5 mL, 158 mmol), and ammonium acetate (1.6 g, 20.8 mmol) in acetic acid (40 mL) and heat to reflux under a nitrogen atmosphere for 17 hours. Cool to room temperature and concentrate. Dissolve in isopropyl alcohol (150 mL) and chloroform (750 mL) and add silica gel (108 g). To the resulting slurry, slowly add sodium borohydride (7.8 g, 206 mmol). Stir the mixture for 17 hours, filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes), to give the desired compound as an orange oil. heat to reflux under a nitrogen atmosphere for 17 hours concentrate Dissolve in isopropyl alcohol (150 mL) chloroform (750 mL) and add silica gel (108 g) filter concentrate purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

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

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

Procedure: Dissolve 2-ethyl benzaldehyde (7 mL, 53.2 mmol), nitromethane (8.5 mL, 158 mmol), and ammonium acetate (1.6 g, 20.8 mmol) in acetic acid (40 mL) and heat to reflux under a nitrogen atmosphere for 17 hours. Cool to room temperature and concentrate. Dissolve in isopropyl alcohol (150 mL) and chloroform (750 mL) and add silica gel (108 g). To the resulting slurry, slowly add sodium borohydride (7.8 g, 206 mmol). Stir the mixture for 17 hours, filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes), to give the desired compound as an orange oil. heat to reflux under a nitrogen atmosphere for 17 hours concentrate Dissolve in isopropyl alcohol (150 mL) chloroform (750 mL) and add silica gel (108 g) filter concentrate purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

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

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 4-amino-benzoic acid methyl ester (1 g, 6 mmol) and 2-ethyl-benzaldehyde (1.2 g, 8.9 mmol) in acetonitrile (40 mL) were added isobutene (1.7 mL, 24 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (0.55 g, 0.9 mmol). The resulting mixture was stirred at 85° C. for 16 h in sealed tube. The mixture was diluted with ethyl acetate (100 mL) and washed with water (50 mL×2) and brine (50 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(2-ethyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1 g, 49%) as a light yellow solid: MS (ESI) M+1=337.0. washed with water (50 mL×2) and brine (50 mL×2) dried over anhydrous sodium sulfate The solvent was removed in vacuo the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether)

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 4-amino-benzoic acid methyl ester (1 g, 6 mmol) and 2-ethyl-benzaldehyde (1.2 g, 8.9 mmol) in acetonitrile (40 mL) were added isobutene (1.7 mL, 24 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (0.55 g, 0.9 mmol). The resulting mixture was stirred at 85° C. for 16 h in sealed tube. The mixture was diluted with ethyl acetate (100 mL) and washed with water (50 mL×2) and brine (50 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(2-ethyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1 g, 49%) as a light yellow solid: MS (ESI) M+1=337.0. washed with water (50 mL×2) and brine (50 mL×2) dried over anhydrous sodium sulfate The solvent was removed in vacuo the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether)

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

Procedure: A stirred suspension of 2-ethylbenzaldehyde (0.98 mL, 7.45 mmol) and AlCl3 (1.74 g, 13 mmol) in DCM (4.5 mL) at 0° C. is treated with a solution of Br2 (0.38 mL, 7.45 mmol) in DCM (4.5 mL) dropwise over 6 h then stirred 16 h at RT. After this time, the reaction mixture is poured over ice-water (50 mL), the layers separated and the aqueous layer extracted with DCM (3×50 mL). The organic phases are combined and washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4 then the solvents removed in vacuo. Purification by column chromatography (gradient elution—100% heptane increasing to 10% EtOAc in heptane) gives the title compound. the layers separated the aqueous layer extracted with DCM (3×50 mL) washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL) dried over Na2SO4 the solvents removed in vacuo Purification by column chromatography (gradient elution—100% heptane increasing to 10% EtOAc in heptane)

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

Procedure: A stirred suspension of 2-ethylbenzaldehyde (0.98 mL, 7.45 mmol) and AlCl3 (1.74 g, 13 mmol) in DCM (4.5 mL) at 0° C. is treated with a solution of Br2 (0.38 mL, 7.45 mmol) in DCM (4.5 mL) dropwise over 6 h then stirred 16 h at RT. After this time, the reaction mixture is poured over ice-water (50 mL), the layers separated and the aqueous layer extracted with DCM (3×50 mL). The organic phases are combined and washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4 then the solvents removed in vacuo. Purification by column chromatography (gradient elution—100% heptane increasing to 10% EtOAc in heptane) gives the title compound. the layers separated the aqueous layer extracted with DCM (3×50 mL) washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL) dried over Na2SO4 the solvents removed in vacuo Purification by column chromatography (gradient elution—100% heptane increasing to 10% EtOAc in heptane)