Reaktion #51135

Reaktionsgleichung

Hydroxyester

methyl 4-(3-hydroxypropyl)bicyclo[2.2.2]octane-1-carboxylate

pyridine

methanesulfonyl chloride

→

methyl 4-{3-[(methylsulfonyl)oxy]propyl}bicyclo-[2.2.2]octane-1-carboxylate

Lösungsmittel

methylene chloride

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 1N aqueous HCl, saturated aqueous sodium bicarbonate, and brine
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Sonstigeevaporated

Vorschrift

Hydroxyester 11-4 (430 mg, 1.9 mmol) was dissolved in 2.5 mL of anhydrous methylene chloride under nitrogen atmosphere, treated with pyridine (0.5 mL) and methanesulfonyl chloride (0.368 mL, 4.8 mmol) and stirred for 4 h at room temperature. The mixture was diluted with 100 mL of ethyl acetate and washed with 1N aqueous HCl, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated. The crude methyl 4-{3-[(methylsulfonyl)oxy]propyl}bicyclo-[2.2.2]octane-1-carboxylate (11-5) thus afforded was used without purification in the next reaction. 1H NMR (500 MHz, CDCl3): δ 4.22 (2H, t, J=7.5 Hz), 3.68 (3H, s), 3.04 (3H, s), 1.82 (6H, m), 1.70 (2H, m), 1.44 (6H, m), 1.24 (2H, m) ppm.

Quelle