(2-butyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone

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

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

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

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

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

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (0.500 g, 17.0 mmol) and lithium aluminum hydride (34.0 mmol) in THF (84 mL) was refluxed for 3 h. The reaction was cooled to −10° C., and carefully quenched with 0.1N NaOH and H2O. The aqueous solution was extracted with ether and concentrated. Purification on silica gel gave the title compound as a white solid, mp 94-96° C. (DMSO-d6) δ0.90 (t, 3H), 1.35 (sextet, 2H), 1.64 (quintet, 2H), 2.84 (t, 2H), 5.67 (d, 1H), 5.87 (d, 1H), 6.69 (d, 2H), 7.07 (t, 1H), 7.15 (dt, 1H), 7.22 (d, 2H), 7.40-7.43 (m, 2H), 9.24 (s, 1H). IR (KBr) 3350, 2950, 1610, 1510 and 1450 cm−1. mass spectrum (EI) m/z 296 (M+). Anal. Calcd. for C19H20O3: C, 77.00; H, 6.80; N, 0.00. Found: C, 75.63; H, 6.86; N, 0.04. was refluxed for 3 h carefully quenched with 0.1N NaOH and H2O The aqueous solution was extracted with ether concentrated Purification on silica gel

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (0.500 g, 17.0 mmol) and lithium aluminum hydride (34.0 mmol) in THF (84 mL) was refluxed for 3 h. The reaction was cooled to −10° C., and carefully quenched with 0.1N NaOH and H2O. The aqueous solution was extracted with ether and concentrated. Purification on silica gel gave the title compound as a white solid, mp 94-96° C. (DMSO-d6) δ0.90 (t, 3H), 1.35 (sextet, 2H), 1.64 (quintet, 2H), 2.84 (t, 2H), 5.67 (d, 1H), 5.87 (d, 1H), 6.69 (d, 2H), 7.07 (t, 1H), 7.15 (dt, 1H), 7.22 (d, 2H), 7.40-7.43 (m, 2H), 9.24 (s, 1H). IR (KBr) 3350, 2950, 1610, 1510 and 1450 cm−1. mass spectrum (EI) m/z 296 (M+). Anal. Calcd. for C19H20O3: C, 77.00; H, 6.80; N, 0.00. Found: C, 75.63; H, 6.86; N, 0.04. was refluxed for 3 h carefully quenched with 0.1N NaOH and H2O The aqueous solution was extracted with ether concentrated Purification on silica gel

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

Procedure: The title compound was prepared according to the procedure in Example 4 using commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (1.00 g, 3.40 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.61 g, 6.79 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with EtOAc/hexane gave 0.185 g (11%) of the title compound as an off white solid, mp 143-145° C. 1H NMR (DMSO-d6) δ0.76 (t, 3H), 1.12-1.22 (m, 2H), 1.60 (quintet, 2H), 2.69 (t, 2H), 7.21-7.38 (m, 7H), 7.61 (d, 1H), 7.76 (d, 2H), 7.98 (d, 1H). IR (KBr) 2950, 1690, 1600, 1380 and 1150 cm−1. mass spectrum (+ESI) m/z 495 (M+H). Anal. Calcd. for C26H22O8S.0.2H2O: C, 62.24; H, 4.58; N, 0.00. Found: C, 62.38; H, 4.59; N, 0.13. The title compound was prepared Purification on 2% H3PO4/MeOH treated silica gel eluting with EtOAc/hexane

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

Procedure: The title compound was prepared according to the procedure in Example 4 using commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (1.00 g, 3.40 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.61 g, 6.79 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with EtOAc/hexane gave 0.185 g (11%) of the title compound as an off white solid, mp 143-145° C. 1H NMR (DMSO-d6) δ0.76 (t, 3H), 1.12-1.22 (m, 2H), 1.60 (quintet, 2H), 2.69 (t, 2H), 7.21-7.38 (m, 7H), 7.61 (d, 1H), 7.76 (d, 2H), 7.98 (d, 1H). IR (KBr) 2950, 1690, 1600, 1380 and 1150 cm−1. mass spectrum (+ESI) m/z 495 (M+H). Anal. Calcd. for C26H22O8S.0.2H2O: C, 62.24; H, 4.58; N, 0.00. Found: C, 62.38; H, 4.59; N, 0.13. The title compound was prepared Purification on 2% H3PO4/MeOH treated silica gel eluting with EtOAc/hexane

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

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

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