Reaktion #88315

Reaktionsgleichung

Benzyl bromide

methyl 2-(2-methoxyphenyl)acetate

THF

Lithium diisopropyl amide

→

desired compound

Ausbeute 35.0%

methyl 2-(2-methoxyphenyl)-3-phenylpropanoate

Ausbeute 35.0%

Lösungsmittel

heptane THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintaining a temperature less than 3° C
2. 2
   Temperaturto gradually warm to room temperature
3. 3
   workup.STIRRINGis stirred for 18 hours
4. 4
   SonstigeThe reaction is quenched with 1N HCl
5. 5
   Extraktionextracted 3 times with equal portions of EtOAc
6. 6
   WaschenThe combined extracts are washed with H2O and brine
7. 7
   Trocknendried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue is purified over silica

Vorschrift

A 500 mL round-bottom flask is charged with methyl 2-(2-methoxyphenyl)acetate (8.496 g, 47 mmol, 1 eq) and THF (200 mL). The homogeneous mixture is cooled to 0° C. in an ice bath. Lithium diisopropyl amide (23.5 mL of a 2.0M solution in heptane/THF) is added, maintaining a temperature less than 3° C. The reaction is stirred 45 minutes at this reduced temperature. Benzyl bromide (5.6 mL, 47 mmol, 1 eq) is added dropwise. The reaction is allowed to gradually warm to room temperature and is stirred for 18 hours. The reaction is quenched with 1N HCl and extracted 3 times with equal portions of EtOAc. The combined extracts are washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. The residue is purified over silica to afford 4.433 g (35%) of the desired compound. ESI+ MS 293 (M+Na).

Quelle