Reacción #1058146

Ecuación de reacción

(2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol

2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde

6-bromo-2,3-dihydrobenzo[1,4]dioxine

n-butyl lithium

→

bis-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanol

Rendimiento 86.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.)

Procedimiento

2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde (0.87 g, 5.28 mmol), 6-bromo-2,3-dihydrobenzo[1,4]dioxine (1.25 g, 5.81 mmol), and n-butyl lithium (2.33 ml, 5.81 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.) to give bis-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanol as an oil (1.37 g, 86%): 1HNMR (CDCl3) 6.87-6.82 (m, 6H, Ar), 5.63 (d, J=3 Hz, 1H, CHOH), 4.22 (s, 8H, 2CH2CH2), 2.19 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Fuente