tert-butyl-(3,4-dihydro-2H-chromen-4-yloxy)-dimethylsilane

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

Procedure: tert-Butyl-chloro-dimethyl-silane (10.54 g, 70 mmol) was added to a CH2Cl2 (200 mL) solution of 4-chromanol (10.00 g, 66.6 mmol), N-methylmorpholine (10.98 mL, 100 mmol) and imidazole (0.20 g, 3 mmol) at 0° C. The mixture was stirred for 3 days at RT. The reaction was diluted with CH2Cl2 (200 mL), washed with dilute HCl and H2O, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. washed with dilute HCl and H2O dried over MgSO4 filtered concentrated in vacuo

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

Procedure: tert-Butyl-chloro-dimethyl-silane (10.54 g, 70 mmol) was added to a CH2Cl2 (200 mL) solution of 4-chromanol (10.00 g, 66.6 mmol), N-methylmorpholine (10.98 mL, 100 mmol) and imidazole (0.20 g, 3 mmol) at 0° C. The mixture was stirred for 3 days at RT. The reaction was diluted with CH2Cl2 (200 mL), washed with dilute HCl and H2O, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. washed with dilute HCl and H2O dried over MgSO4 filtered concentrated in vacuo

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

Procedure: tert-Butyl-chloro-dimethyl-silane (10.54 g, 70 mmol) was added to a CH2Cl2 (200 mL) solution of 4-chromanol (10.00 g, 66.6 mmol), N-methylmorpholine (10.98 mL, 100 mmol) and imidazole (0.20 g, 3 mmol) at 0° C. The mixture was stirred for 3 days at RT. The reaction was diluted with CH2Cl2 (200 mL), washed with dilute HCl and H2O, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. washed with dilute HCl and H2O dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:3.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Butyllithium was added to an Et2O (80 mL) solution of tert-butyl-(chroman-4-yloxy)-dimethyl-silane (6.21 g, 23.5 mmol) at −80° C. After stirring the mixture at 3° C. for 15 h, DMF (10 mL) was added at 0° C. Following a 30 min stirring at RT, the reaction was quenched with saturated NH4Cl solution. The reaction was diluted with Et2O (200 mL) and washed with brine. The organic phase was dried over MgSO41 filtered, and concentrated in vacuo to provide the crude compound (40% conversion by 1H NMR) which was purified by column chromatography (silica, 0 to 10% ether in hexane) to provide the title compound. Following a 30 min stirring at RT the reaction was quenched with saturated NH4Cl solution The reaction was diluted with Et2O (200 mL) washed with brine The organic phase was dried over MgSO41 filtered concentrated in vacuo to provide the crude compound (40% conversion by 1H NMR) which was purified by column chromatography (silica, 0 to 10% ether in hexane)