tert-butyl cyclopentanecarboxylate

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

Procedure: Cool a metal bomb in a CO2 -acetone bath and charge with isobutylene (150 ml), cyclopentanecarboxylic acid (29.4 g, 0.26 mol), t-butanol (4 ml) and H2SO4 (1 ml). Remove the bomb from the cold-bath, seal and stir for 3 days. Cool the bomb in a CO2 -acetone bath, open to the atmosphere and evaporate isobutylene under a stream of N2 while allowing the reaction mixture to attain R.T. Add Et2O (300 ml) and wash the mixture with sat'd NaHCO3 (300 ml) and sat'd NaCl, then dry (MgSO4), filter and concentrate to obtain a colorless oil (41.5 g, 95%) which is used without further purification. 1H Nmr (CDCl3) δ2.58 (1H, m), 1.90-1.35 (8H, m), 1.39 (9H, s). Cool a metal bomb in a CO2 -acetone bath Remove the bomb from the cold-bath seal Cool the bomb in a CO2 -acetone bath open to the atmosphere and evaporate isobutylene under a stream of N2 to attain R.T Add Et2O (300 ml) and wash the mixture with sat'd NaHCO3 (300 ml) dry (MgSO4) filter concentrate

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

Procedure: Cool a metal bomb in a CO2 -acetone bath and charge with isobutylene (150 ml), cyclopentanecarboxylic acid (29.4 g, 0.26 mol), t-butanol (4 ml) and H2SO4 (1 ml). Remove the bomb from the cold-bath, seal and stir for 3 days. Cool the bomb in a CO2 -acetone bath, open to the atmosphere and evaporate isobutylene under a stream of N2 while allowing the reaction mixture to attain R.T. Add Et2O (300 ml) and wash the mixture with sat'd NaHCO3 (300 ml) and sat'd NaCl, then dry (MgSO4), filter and concentrate to obtain a colorless oil (41.5 g, 95%) which is used without further purification. 1H Nmr (CDCl3) δ2.58 (1H, m), 1.90-1.35 (8H, m), 1.39 (9H, s). Cool a metal bomb in a CO2 -acetone bath Remove the bomb from the cold-bath seal Cool the bomb in a CO2 -acetone bath open to the atmosphere and evaporate isobutylene under a stream of N2 to attain R.T Add Et2O (300 ml) and wash the mixture with sat'd NaHCO3 (300 ml) dry (MgSO4) filter concentrate