88928-69-2

Questions And Answer

• Synthesis

  To a solution of β-ketoester 132 (12.6 g, 0.05 mol) in MeOH, NaBH4 (0.97 g, 0.03 mol) was added in portions at 0 ºC. The reaction mixture was stirred at room temperature for 2 hours. MeOH was removed on rotavapor, water was added to it and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to furnish a faint yellow syrup. To the solution of this syrup in DCM, Et3N (10.65 ml, 0.08 mol) was added and cooled to 0 ºC, MsCl (4.35 ml, 0.05 mol) was added drop-wise via syringe at 0 ºC. The reaction mixture was allowed to warm gradually and left overnight. It was observed that the mesylate was formed smoothly and subsequently underwent elimination under reaction conditions to afford the desired olefin. The reaction mixture was washed with water, brine and dried over anhydrous Na2SO4. The organic phase was filtered and concentrated under reduced pressure and the resultant residue was chromatographed over silica gel to furnish olefin 127 as a pale yellow syrup (8.84 g).
  
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