tert-butyl 2-[2-[2-[2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium azide (1.5 g, 23 mmol) was added to a solution of compound 3 (1.9 g, 4.1 mmol) in dry DMF (50 mL) and the resulting mixture was stirred at 80° C. overnight. The reaction mixture was concentrated in vacuo and then triturated with CH2Cl2 (20 mL) and filtered to remove sodium azide. The filtrate was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (200 g) and eluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v) to afford compound 4 as a colorless oil (1.0 g, 57%). The reaction mixture was concentrated in vacuo triturated with CH2Cl2 (20 mL) filtered to remove sodium azide The filtrate was concentrated in vacuo eluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v)

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

Procedure: Carbon tetrabromide (9.0 g, 27 mmol) and triphenyl phosphine (1.2 g, 4.5 mmol) were added to a solution of compound 2 (1.8 g, 4.5 mmol) in dry CH2Cl2 (100 mL). After stirring the reaction mixture for 5 h, the solvent was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (200 g) and eluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v) to afford compound 3 as a colorless oil (1.9 g, 91%). the solvent was concentrated in vacuo eluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v)