6-(1,3-dioxolan-2-ylmethyl)-3,4-dihydroisochromen-1-one

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

Procedure: 6-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-1H-isochromen-1-one (4.42 g, 18.9 mmol) was dissolved in dioxane (25 mL) and treated with 3 M HCl (40 mL). The reaction mixture was stirred at room temperature over night, then was warmed to 50° C. for 2 hours to drive the reaction to completion (however this led to increased side product production based on LCMS). Ethyl acetate was added and the layers were separated. The aqueous layer was extracted again with ethyl acetate, and the combined organic layers were washed with brine and dried over MgSO4 to afford the title compound. was warmed to 50° C. for 2 hours the reaction to completion (however to increased side product production the layers were separated The aqueous layer was extracted again with ethyl acetate the combined organic layers were washed with brine dried over MgSO4

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

Procedure: 6-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-1H-isochromen-1-one (4.42 g, 18.9 mmol) was dissolved in dioxane (25 mL) and treated with 3 M HCl (40 mL). The reaction mixture was stirred at room temperature over night, then was warmed to 50° C. for 2 hours to drive the reaction to completion (however this led to increased side product production based on LCMS). Ethyl acetate was added and the layers were separated. The aqueous layer was extracted again with ethyl acetate, and the combined organic layers were washed with brine and dried over MgSO4 to afford the title compound. was warmed to 50° C. for 2 hours the reaction to completion (however to increased side product production the layers were separated The aqueous layer was extracted again with ethyl acetate the combined organic layers were washed with brine dried over MgSO4

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

Procedure: 6-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-1H-isochromen-1-one (4.42 g, 18.9 mmol) was dissolved in dioxane (25 mL) and treated with 3 M HCl (40 mL). The reaction mixture was stirred at room temperature over night, then was warmed to 50° C. for 2 h to drive the reaction to completion (however this led to increased side product production based on LCMS). Ethyl acetate was added and the layers were separated. The aqueous layer was extracted again with ethyl acetate, and the combined organic layers were washed with brine and dried over MgSO4 to afford the title compound. was warmed to 50° C. for 2 h the reaction to completion (however to increased side product production the layers were separated The aqueous layer was extracted again with ethyl acetate the combined organic layers were washed with brine dried over MgSO4

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

Procedure: 6-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-1H-isochromen-1-one (4.42 g, 18.9 mmol) was dissolved in dioxane (25 mL) and treated with 3 M HCl (40 mL). The reaction mixture was stirred at RT over night, and then was warmed to 50° C. for 2 hrs to drive the reaction to completion. Ethyl acetate was added and the layers were separated. The aqueous layer was extracted again with ethyl acetate, and the combined organic layers were washed with brine and dried over MgSO4 to afford the title compound. LCMS: m/z 191 (M+1)+. was warmed to 50° C. for 2 hrs the reaction to completion the layers were separated The aqueous layer was extracted again with ethyl acetate the combined organic layers were washed with brine dried over MgSO4

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-bromo-3,4-dihydro-1H-isochromen-1-one (10 g, 44 mmol) was combined with tri-t-butyl phosphonium tetrafluoroborate (256 mg, 0.881 mmol), palladium (II) acetate (99 mg, 0.44 mmol) and commercially available bromo(1,3-dioxolan-2-ylmethyl)zinc solution (0.5 M, 97 mL, 48 mmol) in DMF (100 mL), and the mixture was degassed three times by alternating vacuum and nitrogen purge. The mixture was then heated at 85° C. for 6 h, then was stirred at RT overnight. Ethyl acetate and ether were added and the mixture was washed with water. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, and washed twice with water and once with brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by MPLC (silica) eluting with ethyl acetate in hexanes to afford the title compound. LCMS: m/z 235 (M+1)+. the mixture was degassed three times purge Ethyl acetate and ether were added the mixture was washed with water The aqueous layer was extracted with ethyl acetate washed twice with water and once with brine The organic layer was dried over MgSO4 filtered concentrated The crude product was purified by MPLC (silica) eluting with ethyl acetate in hexanes