Reaction equation
[CH3:1][C:2](=[O:5])[CH:3]=[CH2:4].C(N(CC)CC)C.[CH3:13][Si:14](OS(C(F)(F)F)(=O)=O)([CH3:16])[CH3:15]>C(Cl)Cl>[CH3:13][Si:14]([CH3:16])([CH3:15])[O:5][C:2]([CH:3]=[CH2:4])=[CH2:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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. 4 ml of water are added to the mixture and the aqueous phase is extracted with methylene chloride, the organic phase is washed with a saturated solution of NaHCO3, water, a saturated solution of NaCl and is dried on Na2SO4. After filtration the solvent is removed and 59 mg of crude product are obtained. The product is purified by flash chromatography on silica gel column (FCC) eluting with methylene chloride and triethylamine 1%. 18 mg of the wanted product are obtained (crystals). M.p.: 53-54° C. Yield 25%.
Workup
- customequipped with magnetic stirrer
Sources & evidence
- ORD record
- ord-9f6aa8c226dd4813bde171c914615be6
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06303622B1
Linked notes
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