반응 #63016

반응 방정식

benzothiophene

Butyl lithium

N-(dimethoxyacetyl)morpholine

→

2-(Dimethoxyacetyl)benzothiophene

용매

THF

THF

반응 조건

후처리

1. 1
   온도maintaining 0°-5°
2. 2
   온도cooled to -75° C.
3. 3
   온도maintaining -75° to -70°
4. 4
   기타The reaction was quenched
5. 5
   workup.ADDITIONby adding to 300 ml
6. 6
   기타The organic layer was separated
7. 7
   세척washed with brine
8. 8
   건조dried over MgSO4
9. 9
   workup.DISTILLATION, which was distilled
10. 10
    기타to yield
11. 11
    기타purified title product, 8.00 g

실험 절차

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).

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