2-cyclopentyloxy-3-methoxybenzaldehyde

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:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-hydroxy-3-methoxy-benzaldehyde (10 g, 6.57 mmoles), K2CO3 (18.16 g, 131 mmoles), cyclopentyl-bromide (14.05 ml, 131 mmoles) in absolute ethanol (150 ml) under nitrogen was refluxed under stirring for 55 hours. The mixture was diluted with water, thrice extracted in ethyl acetate, washed with water, anhydrified over Na2SO4 and evaporated to dryness, the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5) to give 8.9 g of the title product (yield: 61%). was refluxed extracted in ethyl acetate washed with water evaporated to dryness the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5)

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

Procedure: To the stirred solution of 2-(cyclopentyloxy)-3-methoxybenzaldehyde (3 g, 13.636 mmol) in ethanol was added hydroxylamine hydrochloride (1.758 g, 27.277 mmol) and aqueous solution of sodium hydroxide (18 ml, 34.091 mmol). The reaction mixture was refluxed for 6 h under nitrogen atmosphere. The solvent was evaporated under reduced pressure and the reaction mixture diluted with water. The product was extracted using chloroform (3×200 ml), combined organic layers washed with water (3×100 ml), brine (50 ml), dried (Na2SO4), filtered and concentrated under vacuum to yield 3.12 g of the product. 1H NMR (300 MHz, CDCl3) δ 1.58-1.64 (m, 4H), 1.66-1.72 (m, 4H), 3.84 (s, 3H), 4.86 (br s, 1H), 6.89 (d, J=8.1 Hz, 1H), 6.99 (t, J=7.8 Hz, 1H), 7.31 (d, J=7.8 Hz, 1H), 8.43 (s, 1H). The reaction mixture was refluxed for 6 h under nitrogen atmosphere The solvent was evaporated under reduced pressure the reaction mixture diluted with water The product was extracted washed with water (3×100 ml), brine (50 ml) dried (Na2SO4) filtered concentrated under vacuum

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

Procedure: A mixture of 2-hydroxy-3-methoxy-benzaldehyde (10 g, 6.57 mmoles), K2CO3 (18.16 g, 131 mmoles), cyclopentyl-bromide (14.05 ml, 131 mmoles) in absolute ethanol (150 ml) under nitrogen was refluxed under stirring for 55 hours. The mixture was diluted with water, thrice extracted in ethyl acetate, washed with water, anhydrified over Na2SO4 and evaporated to dryness, the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5) to give 8.9 g of the title product (yield: 61%). was refluxed extracted in ethyl acetate washed with water evaporated to dryness the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5)

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

Procedure: A mixture of 2-hydroxy-3-methoxy-benzaldehyde (10 g, 6.57 mmoles), K2CO3 (18.16 g, 131 mmoles), cyclopentyl-bromide (14.05 ml, 131 mmoles) in absolute ethanol (150 ml) under nitrogen was refluxed under stirring for 55 hours. The mixture was diluted with water, thrice extracted in ethyl acetate, washed with water, anhydrified over Na2SO4 and evaporated to dryness, the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5) to give 8.9 g of the title product (yield: 61%). was refluxed extracted in ethyl acetate washed with water evaporated to dryness the yielded oil was purified by flash chromatography on silica gel (eluent petrolatum/ethyl acetate 95:5)

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:; See reaction.notes.procedure_details.

Procedure: This compound was prepared as described in Intermediate 1 by the reaction of 2-(cyclopentyloxy)-3-methoxybenzaldehyde (1.318 g, 5.984 mmol) with 5-ethyloxycarbonylimidazo[2,1-b][1,3]thiazol-6-yl-methyl(triphenyl)phosphonium bromide (3.0 g, 5.440 mmol) in the presence of sodium hydride (239 mg, 5.984 mmol) in anhydrous DMSO (20 mL) to give 1.610 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40 (t, J=6.9 Hz, 3H), 1.54-1.65 (m, 4H), 1.78-1.85 (m, 4H), 3.81 (s, 3H), 4.39 (q, J=7.2 Hz, 2H), 4.83-4.86 (m, 1H), 6.99-7.02 (m, 1H), 7.09 (t, J=8.1 Hz, 1H), 7.21-7.25 (m, 1H), 7.46 (d, J=4.5 Hz, 1H), 7.67 (d, J=16.2 Hz, 1H), 7.88 (d, J=16.2 Hz, 1H), 8.12 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 413.27 (M+H)+. This compound was prepared