pent-4-ene-1-sulfonyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Phosphorus oxychloride (570.02 g) was added to sodium 4-pentene-1-sulfonate (199.18 g) at room temperature. After reflux for 3 hours, the solution was cooled in an ice bath. The reaction solution was added gradually to a large amount of ice water. After extraction with diethyl ether, the organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure to obtain 4-pentene-1-sulfonyl chloride (106.31 g) as dark brown oil. After reflux for 3 hours the solution was cooled in an ice bath After extraction with diethyl ether the organic layer was washed with brine dried with magnesium sulfate concentrated under reduced pressure

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

Procedure: Phosphorus oxychloride (570.02 g) was added to sodium 4-pentene-1-sulfonate (199.18 g) at room temperature. After reflux for 3 hours, the solution was cooled in an ice bath. The reaction solution was added gradually to a large amount of ice water. After extraction with diethyl ether, the organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure to obtain 4-pentene-1-sulfonyl chloride (106.31 g) as dark brown oil. After reflux for 3 hours the solution was cooled in an ice bath After extraction with diethyl ether the organic layer was washed with brine dried with magnesium sulfate concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 32 (115 mg, 0.196 mmol) was dissolved in EtOAc (5 mL) cooled to 0° C. and treated with anhydrous HCl gas for 10 min. The reaction mixture was then concentrated to give a solid. The solid was dissolved in DMF (2 mL) and DIPEA (0.1 mL, 0.57 mmol) was added. The reaction was cooled to 10° C. and 4-pentenesulfonyl chloride (35 mg, 0.20 mmol) (Culshaw, P. N.; Walton, J. C., J. Chem. Soc., Perkin Trans. 2 (1991), 8, p 1201) was then added. The mixture was stirred at RT for 30 min, quenched with aqueous NaHCO3 and extracted with EtOAc. The EtOAc extract was dried over NaSO4, filtered, concentrated to an oil and chromatographed on silica to give 33 (94 mg, 78% yield) as a foam. LRMS (M+1)+=620. The reaction mixture was then concentrated to give a solid The reaction was cooled to 10° C. quenched with aqueous NaHCO3 extracted with EtOAc The EtOAc extract was dried over NaSO4 filtered concentrated to an oil chromatographed on silica