Benzyl Alcohol → (3aR,6aS)-2-(Benzyloxy)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

Beteiligte Stoffe

Reaktionsschritte

Purified lactol 7 (591.5 mg, 3.84 mmol, 1 eq.), was dissolved in CH2Cl2 (7 ml) and stirred at r.t. Benzyl alcohol (794.1 μL, 7.68 mmol, 2 eq.) was added via syringe and amberlyst 15 (56.5 mg) and MgSO4 (1.16 g) were added as solids. The reaction mixture was stirred at r.t. for 36 h. The reaction mixture was filtered through a sinter funnel and the solids washed with CH2Cl2 (2×10 ml). The filtrate was concentrated under reduced pressure to give the crude material which was purified by column chromatography eluting with petrol/EtOAc (9:1) to give the benzyl acetal 56 (as an approximately 1.5:1 mixture of diasteroisomers, 657.8 mg, 70%) as pale yellow oil.

Herkunft & Nachweise