Acetic Acid → 6-Benzyloxymethyl-2-methyl-5,6-dihydro-4H-pyran-4-one

Beteiligte Stoffe

Reaktionsschritte

A solution of 10.4 g of the aldehyde from Step 1 in 250 ml of THF was cooled to 0° C. and 1.0 eq. of freshly prepared MgBr2 was added dropwise. The mixture was warmed to r.t. and 40.6 g of 1,3-bis(trimethylsilyloxy)-1,3-butadiene (Emde, et al., Synthesis, p. 6 (1982)) was added. After 3 h., 50% aqueous HOAc was added and the mixture was stirred 10 min. and then extracted with Et2O (2x). After the ether was evaporated, the resultant oil was taken back up in 300 ml of CH2Cl2 and 12 ml of TFA. After 3 hours, the solution was washed with H2O, saturated NaHCO3, brine and finally dried over MgSO4. After flash chromatography, 9.5 g (60%) of the title compound was obtained.

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