lead(2+);tetraacetate

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

Procedure: To a solution of lead(IV)acetate (4.0 g, 0.0089 mol) and mercury(II)acetate (139 mg, 0.45 mmol) in chloroform (12 ml) at 50° C. is added 5-bromo-2-cyclopropylphenyl boronic acid (2.0 g, 0.0083 mol), and the solution is heated at this temperature for 5 hours. After cooling to room temperature the suspension is further cooled to 0° C. and anhydrous potassium carbonate (1.8 g) is added with rapid stirring for 2 minutes. The reaction mixture is then filtered (washing with additional chloroform), and the filtrate is concentrated to half its original volume and the crude product is precipitated with hexanes. Further concentration then filtration affords 5-bromo-2-cyclopropylphenyl lead triacetate as a beige solid. the solution is heated at this temperature for 5 hours is further cooled to 0° C. The reaction mixture is then filtered (washing with additional chloroform) the filtrate is concentrated to half its original volume the crude product is precipitated with hexanes Further concentration filtration

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90% lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution, which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90%/0 lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90% lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution, which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated

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

Procedure: To a solution of lead(IV)acetate (4.0 g, 0.0089 mol) and mercury(II)acetate (139 mg, 0.45 mmol) in chloroform (12 ml) at 50° C. is added 5-bromo-2-cyclopropylphenyl boronic acid (2.0 g, 0.0083 mol), and the solution is heated at this temperature for 5 hours. After cooling to room temperature the suspension is further cooled to 0° C. and anhydrous potassium carbonate (1.8 g) is added with rapid stirring for 2 minutes. The reaction mixture is then filtered (washing with additional chloroform), and the filtrate is concentrated to half its original volume and the crude product is precipitated with hexanes. Further concentration then filtration affords 5-bromo-2-cyclopropylphenyl lead triacetate as a beige solid. the solution is heated at this temperature for 5 hours is further cooled to 0° C. The reaction mixture is then filtered (washing with additional chloroform) the filtrate is concentrated to half its original volume the crude product is precipitated with hexanes Further concentration filtration

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90% lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution, which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated

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

Procedure: To a solution of lead(IV)acetate (4.0 g, 0.0089 mol) and mercury(II)acetate (139 mg, 0.45 mmol) in chloroform (12 ml) at 50° C. is added 5-bromo-2-cyclopropylphenyl boronic acid (2.0 g, 0.0083 mol), and the solution is heated at this temperature for 5 hours. After cooling to room temperature the suspension is further cooled to 0° C. and anhydrous potassium carbonate (1.8 g) is added with rapid stirring for 2 minutes. The reaction mixture is then filtered (washing with additional chloroform), and the filtrate is concentrated to half its original volume and the crude product is precipitated with hexanes. Further concentration then filtration affords 5-bromo-2-cyclopropylphenyl lead triacetate as a beige solid. the solution is heated at this temperature for 5 hours is further cooled to 0° C. The reaction mixture is then filtered (washing with additional chloroform) the filtrate is concentrated to half its original volume the crude product is precipitated with hexanes Further concentration filtration

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90% lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution, which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90% lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution, which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90%/0 lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90% lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution, which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%). The mixture was cooled the triethylorthoformate removed under reduced pressure The residue was dissolved in CHCl3 the remaining precipitate filtered off The CHCl3 solution was then washed with water evaporated to yield the crude ester was evaporated under reduced pressure the aqueous solution washed with diethylether (3×25 ml) washed again with diethylether (3×25 ml) The combined fractions from the second ether wash were dried (Na2SO4) evaporated