5-(2-methoxyphenyl)furan-2-carbaldehyde

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

Procedure: To a mixture of 3-ethyloxazolidine-2,4-dithione 6 (79 mg, 0.49 mmol), 5-(2-methoxyphenyl)-2-furaldehyde 9 (99 mg, 0.49 mmol) and sodium acetate (201 mg, 2.45 mmol) was added acetic acid (5 mL). As more of the desired product was formed, the reaction mixture color turned to a very red solution. The reaction mixture was refluxed overnight, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. Flash column chromatography afforded the desired product 2 (M103) in 95% yield (160 mg, purple solid).

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

Procedure: To a mixture of 3-ethyloxazolidine-2,4-dithione 6 (79 mg, 0.49 mmol), 5-(2-methoxyphenyl)-2-furaldehyde 9 (99 mg, 0.49 mmol) and sodium acetate (201 mg, 2.45 mmol) was added acetic acid (5 mL). As more of the desired product was formed, the reaction mixture color turned to a very red solution. The reaction mixture was refluxed overnight, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. Flash column chromatography afforded the desired product 2 (M103) in 95% yield (160 mg, purple solid).

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

Procedure: To a benzene (10 mL) solution of 5-bromo-2-furaldehyde 7 (350 mg, 2.0 mmol) and 2-methoxyphenylboronic acid 8 (304 mg, 2.0 mmol) was added tetrakis(triphenylphosphine)-palladium(0) (69.4 mg, 0.06 mmol) and sat. aq. K2CO3 solution (4.94 ml, 4.0 mmol) at 21° C. under an argon atmosphere. The reaction mixture was refluxed for 2 h. The mixture was then cooled and diluted with ethyl acetate (100 mL). The organic layer was washed with water (2×20 mL), then dried with brine and MgSO4 and concentrated in vacuo. Flash column chromatography on silica gel (hexane:ethyl acetate=20:1) of the residue afforded 5-(2-methoxyphenyl)-2-furaldehyde 9 in 65% yield (265 mg, yellow oil). 1H NMR (400 MHz, CDCl3): δ 9.65 (s, 1H), 8.05 (dd, J=8.0, 2.0 Hz, 1H), 7.39-7.35 (m, 1H), 7.33 (d, J=3.6 Hz, 1H), 7.14 (d, J=4.0 Hz, 1H), 7.07 (dt, J=7.2, 0.8 Hz, 1H), 7.00 (bd, J=8.0 Hz, 1H), 3.97 (s, 3H). The reaction mixture was refluxed for 2 h The mixture was then cooled The organic layer was washed with water (2×20 mL) dried with brine and MgSO4 concentrated in vacuo

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

Procedure: To a benzene (10 mL) solution of 5-bromo-2-furaldehyde 7 (350 mg, 2.0 mmol) and 2-methoxyphenylboronic acid 8 (304 mg, 2.0 mmol) was added tetrakis(triphenylphosphine)-palladium(0) (69.4 mg, 0.06 mmol) and sat. aq. K2CO3 solution (4.94 ml, 4.0 mmol) at 21° C. under an argon atmosphere. The reaction mixture was refluxed for 2 h. The mixture was then cooled and diluted with ethyl acetate (100 mL). The organic layer was washed with water (2×20 mL), then dried with brine and MgSO4 and concentrated in vacuo. Flash column chromatography on silica gel (hexane:ethyl acetate=20:1) of the residue afforded 5-(2-methoxyphenyl)-2-furaldehyde 9 in 65% yield (265 mg, yellow oil). 1H NMR (400 MHz, CDCl3): δ 9.65 (s, 1H), 8.05 (dd, J=8.0, 2.0 Hz, 1H), 7.39-7.35 (m, 1H), 7.33 (d, J=3.6 Hz, 1H), 7.14 (d, J=4.0 Hz, 1H), 7.07 (dt, J=7.2, 0.8 Hz, 1H), 7.00 (bd, J=8.0 Hz, 1H), 3.97 (s, 3H). The reaction mixture was refluxed for 2 h The mixture was then cooled The organic layer was washed with water (2×20 mL) dried with brine and MgSO4 concentrated in vacuo

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

Procedure: To a benzene (10 mL) solution of 5-bromo-2-furaldehyde 7 (350 mg, 2.0 mmol) and 2-methoxyphenylboronic acid 8 (304 mg, 2.0 mmol) was added tetrakis(triphenylphosphine)-palladium(0) (69.4 mg, 0.06 mmol) and sat. aq. K2CO3 solution (4.94 ml, 4.0 mmol) at 21° C. under an argon atmosphere. The reaction mixture was refluxed for 2 h. The mixture was then cooled and diluted with ethyl acetate (100 mL). The organic layer was washed with water (2×20 mL), then dried with brine and MgSO4 and concentrated in vacuo. Flash column chromatography on silica gel (hexane:ethyl acetate=20:1) of the residue afforded 5-(2-methoxyphenyl)-2-furaldehyde 9 in 65% yield (265 mg, yellow oil). 1H NMR (400 MHz, CDCl3): δ 9.65 (s, 1H), 8.05 (dd, J=8.0, 2.0 Hz, 1H), 7.39-7.35 (m, 1H), 7.33 (d, J=3.6 Hz, 1H), 7.14 (d, J=4.0 Hz, 1H), 7.07 (dt, J=7.2, 0.8 Hz, 1H), 7.00 (bd, J=8.0 Hz, 1H), 3.97 (s, 3H). The reaction mixture was refluxed for 2 h The mixture was then cooled The organic layer was washed with water (2×20 mL) dried with brine and MgSO4 concentrated in vacuo