methyl 3-cyano-3-(4-hydroxyphenyl)propanoate

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

実験手順: To a 100 mL of two neck RB flask was charged with 2-[4-(hydroxy methyl)phenoxy]-1-phenylethanone (2.5 g, 10.3 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (2.5 g, 12.4 mmol) in 50 mL of toluene. To this added tributylphosphine (3.33 g, 16.5 mmol) at 0° C. and added 1,1′-(Azodicarbonyl)dipiperidine (4.165 g, 16.5 mmol) portion wise over a period of 15 min at 0° C. After 12 h of stirring at RT, the mixture was diluted with n-hexane and stirred for 10 min. Solid formed was filtered off and the filtrate was concentrated to afford crude product which on trituration with ethyl acetate and pet ether gave pure product. (2.5 g yield: 56.1%); 1H NMR (300 MHz, DMSO-d6): δ 8.01-8.03 (d, 2H), 7.67-7.72 (t, 1H), 7.55-7.60 (t, 2H), 7.34-7.37 (d, 4H), 6.96-7.02 (t, 4H), 5.59 (s, 2H), 5.01 (s, 2H), 4.37-4.46 (m, 1H), 3.61 (s, 3H), 3.07-3.16 (m, 1H), 2.90-2.97 (m, 1H). stirred for 10 min Solid formed was filtered off the filtrate was concentrated to afford crude product which on trituration with ethyl acetate and pet ether gave pure product

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

実験手順: To a 100 mL of two neck RB flask was charged with 2-[4-(hydroxy methyl)phenoxy]-1-phenylethanone (2.5 g, 10.3 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (2.5 g, 12.4 mmol) in 50 mL of toluene. To this added tributylphosphine (3.33 g, 16.5 mmol) at 0° C. and added 1,1′-(Azodicarbonyl)dipiperidine (4.165 g, 16.5 mmol) portion wise over a period of 15 min at 0° C. After 12 h of stirring at RT, the mixture was diluted with n-hexane and stirred for 10 min. Solid formed was filtered off and the filtrate was concentrated to afford crude product which on trituration with ethyl acetate and pet ether gave pure product. (2.5 g yield: 56.1%); 1H NMR (300 MHz, DMSO-d6): δ 8.01-8.03 (d, 2H), 7.67-7.72 (t, 1H), 7.55-7.60 (t, 2H), 7.34-7.37 (d, 4H), 6.96-7.02 (t, 4H), 5.59 (s, 2H), 5.01 (s, 2H), 4.37-4.46 (m, 1H), 3.61 (s, 3H), 3.07-3.16 (m, 1H), 2.90-2.97 (m, 1H). stirred for 10 min Solid formed was filtered off the filtrate was concentrated to afford crude product which on trituration with ethyl acetate and pet ether gave pure product

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

実験手順: Compound 105 was synthesized from (4-{[(2Z)-2-cyclopropyl-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.5 g, 2.12 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.44 g, 2.12 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 56.32%); Purity: 84.26%.

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

実験手順: Compound 104 was synthesized from (4-{[(2E)-2-cyclopropyl-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.5 g, 2.12 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.44 g, 2.12 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 44.24%); Purity: 85.80%.

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

実験手順: Compound 104 was synthesized from (4-{[(2E)-2-cyclopropyl-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.5 g, 2.12 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.44 g, 2.12 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 44.24%); Purity: 85.80%.

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

実験手順: Compound 103 was synthesized from (4-{[(2Z)-2-(2,3-dihydro-1H-inden-5-yl)-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.25 g, 0.8 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.214 g, 1.04 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 38.4%); Purity: 95.42%.

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

実験手順: Compound 102 was synthesized from ((4-{[(2Z)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.330 g, 1.0 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.216 g, 1.0 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 56.2%); Purity: 94.55%.

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

実験手順: Compound 102 was synthesized from ((4-{[(2Z)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.330 g, 1.0 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.216 g, 1.0 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 56.2%); Purity: 94.55%.

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

実験手順: Compound 101 was synthesized from (4-{[(2Z)-2-(1H-inden-2-yl)-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.079 g, 0.4 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.11 g, 0.4 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 20.5%); Purity: 97.17%.

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

実験手順: Compound 98 was synthesized from (4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.55 g, 2.03 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.46 g, 2.22 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 30.1%); Purity: 93.18%.

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

実験手順: Compound 98 was synthesized from (4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.55 g, 2.03 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.46 g, 2.22 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 30.1%); Purity: 93.18%.

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

実験手順: To the microwave vial was charged with isomer methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (+ve) (0.5 g, 2.4 mmole) & benzyl alcohol (0.5 mL, 4.8 mmol), was added tributyltinoxide (0.03 g, 5% W/W). Temperature was set 90° C. & energy is fixed at 250 W for 30 mins. After completion of the reaction (monitored by TLC), the RM mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine solution, dried over anhydrous Na2SO4 and evaporated to dryness gave the titled compound (0.040 g, yield: 6.0%). was set 90° C. After completion of the reaction (monitored by TLC) the RM mixture was extracted with ethyl acetate The organic layer was washed with water and saturated brine solution dried over anhydrous Na2SO4 evaporated to dryness