Methyl vinyl ketone → 2-(Trimethylsiloxy)-1,3-butadiene

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Reaction Steps

70 μl (0.86 mmoles) of 3-buten-2-one [compound of formula 5 wherein R1 ═R2═R6═H] and 2 ml of anhydrous CH2Cl2 are charged, at 0° C. under argon in a two-necked round bottom flask equipped with magnetic stirrer and dropping funnel. 170 μl (1.22 mmoles) of triethylamine (distilled on KOH) and 209 μl (1.08 mmoles) of trimethylsilyltrifluorometansulphonate (TMDOTf) (drop by drop) are added to the mixture. In this conditions 2 -(trimethylsilyloxy)-1,3-butadiene [compound 6 wherein R1 =R2═R6═H] is formed “in situ”. The mixture is stirred for 45 minutes and thereafter a solution of 100 mg (0.36 mmoles) of the product from Example 2 in 2 ml of anhydrous CH2Cl2 is added therein, drop by drop, together with 69 μl (0.36 mmoles) of TMSOTf. The mixture is brought to room temperature and after 30 minutes 4 ml of a saturated solution of NAHCO3 are added and the mixture is stirred vigorously for 36 h.

Provenance & Evidence