Reacción #1594929

Ecuación de reacción

tert-butyl 3-hydroxy-2,2-dimethylpropanoate

2-(2-(benzyloxy)ethoxy)ethyl methanesulfonate

2-(2-(Benzyloxy)ethoxy)ethyl methanesulfonate

NaH

→

tert-butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate

Rendimiento 96.5%

tert-Butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate

Rendimiento 96.5%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was quenched with sat. NH4Cl (aq.) (1 mL)
2. 2
   workup.ADDITIONdiluted with water (20 mL)
3. 3
   Lavadowashed with EtOAc (4×20 mL)
4. 4
   SecadoThe combined organic layers were dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product was purified by silica gel chromatography (12 g, 0-40% Et2O in isohexane)

Procedimiento

To a solution of tert-butyl 3-hydroxy-2,2-dimethylpropanoate (353 mg, 2.03 mmol) and 2-(2-(benzyloxy)ethoxy)ethyl methanesulfonate (47) (500 mg, 1.82 mmol) in DMF (6 mL) at 0° C. was added NaH (60 wt % in oil) (109 mg, 2.73 mmol), and the reaction mixture was allowed to stir at RT for 30 min. The reaction mixture was quenched with sat. NH4Cl (aq.) (1 mL) diluted with water (20 mL) and washed with EtOAc (4×20 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (12 g, 0-40% Et2O in isohexane) to afford tert-butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate (48) (619 mg, 96%) as a colourless oil: m/z 375 (M+Na)+ (ES+). 1H NMR (400 MHz, CDCl3) δ: 7.32-7.25 (m, 5H), 4.54 (s, 2H), 3.66-3.56 (m, 8H), 3.41 (s, 2H), 1.40 (s, 8H), 1.10 (s, 6H).

Fuente