2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 5-Methyl-2-phenyl-4-(5-trimethylsilanyl-pent-4-ynyl)-oxazole

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Reaction Steps

Bromide 1-5 (3.2 g, 12.2 mmol) was dissolved in a 1:1 mixture of THF:DMPU (200 mL) and cooled to 0° C. under N2 atmosphere. Trimethylsilyl lithium acetylide (50mL, 25 mmol) was added to the solution via syringe and allowed to equilibrate to 23° C. for 16 hours. The solution was partitioned between water and EtOAc in a separatory funnel. Organic layer was washed with water, brine, and dried over MgSO4. Solvent removed in vacuo and residue chromatographed with 5% EtOAc/hexanes to give 1.9 g of the product as a clear oil (50% yield). NMR CDCl3 (δ): 7.82 (2H, m); 7.27 (3H, m);2.46 (2H, m); 2.20 (3H, s); 2.10 (2H, m); 1.76 (2H, m); 0.01 (9H, s). M+1=298.1

Provenance & Evidence