ethyl 3-[tert-butyl(dimethyl)silyl]oxyhexanoate

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

Procedure: Ethyl 6-((tert-butyldimethylsilyl)oxy)hexanoate 8 (3.08 g) was prepared in 90% yield using ethyl 6-hydroxyhexanoate 7 according to the procedures described for compound 2 in above (see Schemes 1-3).

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

Procedure: Ethyl 6-((tert-butyldimethylsilyl)oxy)hexanoate 8 (3.08 g) was prepared in 90% yield using ethyl 6-hydroxyhexanoate 7 according to the procedures described for compound 2 in above (see Schemes 1-3).

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

Procedure: Ethyl 2-((tert-butyldimethylsilyl)oxy)hexanoate 5 (2.54 g) was prepared in 74% yield using ethyl 2-hydroxyhexanoate 4 according to the procedures described for compound 2 in above (See Schemes 1 and 2).

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

Procedure: n-Butyllithium (6.8 mL of a 1.6M solution in THF, 10.94 mmol) was added to a solution of dimethyl methylphosphonate (1.2 mL, 10.94 mmol) in THF (22 mL) at −78° C. After 0.5 h a solution of the ester 2 (2.0 g, 7.29 mmol) in THF (4 mL) was added. The reaction solution was allowed to warm to room temperature overnight on its own accord. After 16 h the reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 2:1 hex/EtOAc followed by 1:1 hex/EtOAc) afforded 0.93 g (36%) of phosphonate 3 (see Scheme 1). After 16 h the reaction was quenched with saturated aqueous ammonium chloride extracted with EtOAc The organic portion was washed with brine dried (MgSO4) filtered concentrated in vacuo The residue was purified by flash column chromatography (silica gel, 2:1 hex/EtOAc followed by 1:1 hex/EtOAc)

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

Procedure: A solution of ethyl 3-hydroxyhexanoate 1 (2.0 g, 12.5 mmol), imidazole (1.09 g, 18.7 mmol), and tert-butyldimethylsilyl chloride (2.26 g, 15.0 mmol) in DMF (25 mL) was stirred at 23° C. After 16 h the reaction was diluted with Et2O and then washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc) afforded 2.8 g (82%) of silyl ether 2 (see Scheme 1). washed with 1N HCl, saturated aqueous NaHCO3 and brine The organic portion was dried (MgSO4) filtered concentrated in vacuo The residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc)

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

Procedure: A solution of ethyl 3-hydroxyhexanoate 1 (2.0 g, 12.5 mmol), imidazole (1.09 g, 18.7 mmol), and tert-butyldimethylsilyl chloride (2.26 g, 15.0 mmol) in DMF (25 mL) was stirred at 23° C. After 16 h the reaction was diluted with Et2O and then washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc) afforded 2.8 g (82%) of silyl ether 2 (see Scheme 1). washed with 1N HCl, saturated aqueous NaHCO3 and brine The organic portion was dried (MgSO4) filtered concentrated in vacuo The residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc)

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

Procedure: Ethyl 6-((tert-butyldimethylsilyl)oxy)hexanoate 8 (3.08 g) was prepared in 90% yield using ethyl 6-hydroxyhexanoate 7 according to the procedures described for compound 2 in above (see Schemes 1-3).

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

Procedure: Ethyl 2-((tert-butyldimethylsilyl)oxy)hexanoate 5 (2.54 g) was prepared in 74% yield using ethyl 2-hydroxyhexanoate 4 according to the procedures described for compound 2 in above (See Schemes 1 and 2).

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

Procedure: n-Butyllithium (6.8 mL of a 1.6M solution in THF, 10.94 mmol) was added to a solution of dimethyl methylphosphonate (1.2 mL, 10.94 mmol) in THF (22 mL) at −78° C. After 0.5 h a solution of the ester 2 (2.0 g, 7.29 mmol) in THF (4 mL) was added. The reaction solution was allowed to warm to room temperature overnight on its own accord. After 16 h the reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 2:1 hex/EtOAc followed by 1:1 hex/EtOAc) afforded 0.93 g (36%) of phosphonate 3 (see Scheme 1). After 16 h the reaction was quenched with saturated aqueous ammonium chloride extracted with EtOAc The organic portion was washed with brine dried (MgSO4) filtered concentrated in vacuo The residue was purified by flash column chromatography (silica gel, 2:1 hex/EtOAc followed by 1:1 hex/EtOAc)

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

Procedure: A solution of ethyl 3-hydroxyhexanoate 1 (2.0 g, 12.5 mmol), imidazole (1.09 g, 18.7 mmol), and tert-butyldimethylsilyl chloride (2.26 g, 15.0 mmol) in DMF (25 mL) was stirred at 23° C. After 16 h the reaction was diluted with Et2O and then washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc) afforded 2.8 g (82%) of silyl ether 2 (see Scheme 1). washed with 1N HCl, saturated aqueous NaHCO3 and brine The organic portion was dried (MgSO4) filtered concentrated in vacuo The residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc)