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0 °C

A 50 mL round bottom flask was charged with dihydropyran, (3.5 mL, 39 mmol) and pTSA, (7 mg, 0.039 mmol) was added. When the pTSA had dissolved, the solution was cooled to 0° C. in an ice bath and 3-(trimethylsilyl)propargyl alcohol, (5.7 mL, 39 mmol) was added dropwise. It was allowed then allowed to warm slowly to room temperature and held for 1 h. The mixture was added to saturated NaHCO3, (250 mL) extracted with Et2O, (150 mL) (×3), washed with brine, (150 mL), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The material was purified by chromatography eluting with heptane-EtOAc, gradient 0 to 10% EtOAc. 8.5 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.19 (s, 9H) 0.77-0.94 (m, 1H) 1.49-1.59 (m, 1H) 1.57-1.70 (m, 2H) 1.69-1.93 (m, 2H) 3.35-3.63 (m, 1H) 3.78-3.91 (m, 1H) 4.19-4.35 (m, 2H) 4.82 (t, J=3.34 Hz, 1H).

1. additionwas added
2. temperatureto warm slowly to room temperature
3. extractionextracted with Et2O, (150 mL) (×3)
4. washwashed with brine, (150 mL)
5. dry with materialdried (Na2SO4)
6. customthe solvent was evaporated under reduced pressure
7. customThe material was purified by chromatography
8. washeluting with heptane-EtOAc, gradient 0 to 10% EtOAc