Reacción #90243

Ecuación de reacción

nonanedioic acid monomethyl ester

→

methyl 9-hydroxynonanoate

Rendimiento 99.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo prepare 4
2. 2
   Otrothe reaction was quenched with 0.77 M aqueous K2CO3 solution (10 ml) at 0° C
3. 3
   ExtracciónThe product was extracted with diethyl ether (3×20 ml)
4. 4
   Lavadowashed with saturated aqueous NaCl solution
5. 5
   Secadodried over Na2SO4
6. 6
   Concentraciónconcentrated in vacuum

Procedimiento

To prepare 4, a solution of nonanedioic acid monomethyl ester (3) (923 mg, 4.6 mmol) in dry THF (3 ml) at −20° C. was treated with 1 M BH3 in THF (4.6 ml, 4.6 mmol) over 10 minutes. After stirring at room temperature for 4 hours, the reaction was quenched with 0.77 M aqueous K2CO3 solution (10 ml) at 0° C. The product was extracted with diethyl ether (3×20 ml), washed with saturated aqueous NaCl solution, dried over Na2SO4, and concentrated in vacuum to afford methyl 9-hydroxynonanoate (4) (Kai K. et al., Tetrahedron 64:6760-69 (2008), which is hereby incorporated by reference in its entirety) (850 mg, 99% yield) as a colorless oil, which was used directly without any further purification. 1H NMR (400 MHz, chloroform-d1): δ 1.27-1.37 (8H, m), 1.50-1.66 (4H, m), 2.29 (2H, t, J=7.5 Hz), 3.62 (2H, t, J=6.5 Hz), 3.66 (3H, s). See FIG. 75C.

Fuente