Reacción #65502

Ecuación de reacción

potassium iodide

product

4-Tert-Butyldimethylsilyloxymethyl-2-Allylphenol

18-crown-6

methyl 2-bromophenylacetate

→

title compound

Rendimiento 65.4%

Methyl 2-(4-Tert-Butyldimethylsilyloxymethyl -2-Allylphenoxy)-2-Phenylacetate

Rendimiento 65.4%

Disolventes

DMF

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was heated to 80° C. for 0.5 hours
2. 2
   workup.STIRRINGthen stirred at room temperature for 16 hours
3. 3
   ConcentraciónAfter concentration in vacuo
4. 4
   Otrothe residue was partitioned between water and ethyl acetate
5. 5
   LavadoThe combined organic layers were washed with water, brine
6. 6
   Secadodried (MgSO4)
7. 7
   FiltraciónAfter filtration and concentration in vacuo
8. 8
   Otrothe residue was chromatographed on silica (MPLC, ethyl acetate/hexanes (5/95))

Procedimiento

To a suspension of KH (1.3 eq) in DMF (1 mL) was added a solution of the product of Step C (157 mg, 0.566 mmol) in DMF (1 mL), followed by 18-crown-6 (30 mg; 0.2 eq). The reaction mixture was stirred for 5 minutes at room temperature. A solution of methyl 2-bromophenylacetate (168 mg, 0.735 mmol) in DMF (1 mL) was added, followed by a catalytic amount of potassium iodide. The reaction was heated to 80° C. for 0.5 hours then stirred at room temperature for 16 hours. After concentration in vacuo, the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with water, brine, then dried (MgSO4). After filtration and concentration in vacuo, the residue was chromatographed on silica (MPLC, ethyl acetate/hexanes (5/95)) to afford 158 mg (66%) of the title compound (Rf =0.22, 5% ethyl acetate/hexanes).

Fuente