Dimethylformamide → 5-[3-(Dibutyl-pentyl-stannanyl)-allyloxymethyl]-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of rac-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-hydroxymethyl-oxazolidin-2-one (prepared in analogy to Example 1, step 1.i; 0.852 g, 3.4 mmol) and tributyl-(3-chloro-propenyl)-stannane (prepared according to J. Org. Chem. (2000), 65, 7070; 1.2 g, 3.4 mmol) in DMF (20 mL) was cooled to 0° C. and a NaH dispersion (50% in mineral oil, 325 mg, 2 eq.) was added. The mixture was stirred at 0° C. for 30 min and at rt overnight. The volatiles were removed under reduced pressure and the residue partitioned between EA and water. The org. phase was washed with water, dried over MgSO4 and concentrated. The product was purified by FC (Hept/EA 2:1) to give a yellow oil (1.06 g, 53% yield).

Provenance & Evidence