methyl 3-methoxypent-2-enoate

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

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

Procedure: A mixture consisting of 5-benzyloxytryptophol (24.0 g, 0.090 mol), methylene chloride (600 mL), methyl 3-methoxy-2-pentenoate (16.8 g, 0.177 mol) and borontrifluoride etherate (2 mL) is stirred at room temperature for 3 hours. The reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL), dried (MgSO4), filtered and concentrated to give 38.0 g crude product. The crude product is flash chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent to afford 29.0 g pure title compound, m.p. 98°-100° C. The reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL) dried (MgSO4) filtered concentrated to give 38.0 g crude product chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent

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

Procedure: A mixture consisting of 5-benzyloxytryptophol (24.0 g, 0.090 mol), methylene chloride (600 mL), methyl 3-methoxy-2-pentenoate (16.8 g, 0.177 mol) and borontrifluoride etherate (2 mL) is stirred at room temperature for 3 hours. The reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL), dried (MgSO4), filtered and concentrated to give 38.0 g crude product. The crude product is flash chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent to afford 29.0 g pure title compound, m.p. 98°-100° C. The reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL) dried (MgSO4) filtered concentrated to give 38.0 g crude product chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent

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

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

Procedure: To a mixture of methyl propionylacetate (104 g. 0.8 mole) and trimethyl orthoformate 98% (95.3 g, 0.88 mole) was added dropwise 1 ml of concentrated H2SO4 at room temperature and it was allowed to stir overnight. After neutralization with excess anhydrous K2CO3, the solution was filtered and distilled to yield the title ester, b.p. 55° C. (0.55 mm). After neutralization with excess anhydrous K2CO3, the solution was filtered distilled

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

Procedure: A mixture consisting of 5-benzyloxytryptophol (24.0 g, 0.090 mol), methylene chloride (600 mL), methyl 3-methoxy-2-pentenoate (16.8 g, 0.177 mol) and borontrifluoride etherate (2 mL) is stirred at room temperature for 3 hours. The reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL), dried (MgSO4), filtered and concentrated to give 38.0 g crude product. The crude product is flash chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent to afford 29.0 g pure title compound, m.p. 98°-100° C. The reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL) dried (MgSO4) filtered concentrated to give 38.0 g crude product chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent

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