Reacción #63016

Ecuación de reacción

benzothiophene

Butyl lithium

N-(dimethoxyacetyl)morpholine

→

2-(Dimethoxyacetyl)benzothiophene

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintaining 0°-5°
2. 2
   Temperaturacooled to -75° C.
3. 3
   Temperaturamaintaining -75° to -70°
4. 4
   OtroThe reaction was quenched
5. 5
   workup.ADDITIONby adding to 300 ml
6. 6
   OtroThe organic layer was separated
7. 7
   Lavadowashed with brine
8. 8
   Secadodried over MgSO4
9. 9
   workup.DISTILLATION, which was distilled
10. 10
    Otroto yield
11. 11
    Otropurified title product, 8.00 g

Procedimiento

A solution of benzothiophene (7.11 g., 0.053 mol) in 120 ml. dry THF was cooled to 0°. Butyl lithium (35.3 ml. of 1.5M in hexane, 0.053 mol) was added dropwise, maintaining 0°-5°, and the mixture then warmed to ambient temperature for 1.25 hours, cooled to -75° C. and N-(dimethoxyacetyl)morpholine (10.0 g., 0.053 mol) in 50 ml. dry THF added dropwise maintaining -75° to -70°. The reaction was quenched by adding to 300 ml. saturated NH4Cl and 300 ml. ether. The organic layer was separated, washed with brine, dried over MgSO4 and stripped to an oil, 14 g., which was distilled to yield purified title product, 8.00 g., bp 137°-139°/0.25 mm.; tlc Rf 0.23 (6:1 hexane:ethyl acetate), 0.47 (2:1 hexane:ethyl acetate); 1H-nmr 3.6 (s, 6H), 5.2 (s, 1H), 7.3-7.6 (m, 2H), 7.8-8.05 (m, 2H), 8.4 (s, 1H), tlc Rf 0.31 (4:1 hexane:ethyl acetate), 0.47 (2:1 hexane:ethyl acetate).

Fuente