반응 #2066

반응 방정식

N-methoxy-N-methyl-3,3-bis(diethoxyphosphinyl)propionamide

sodium hydride

THF

THF

hydride

→

title compound

수율 54.0%

tetraethyl 3-oxopentane-1,1-bisphosphonate

수율 54.0%

반응 조건

후처리

1. 1
   기타was consumed (~20 minutes)
2. 2
   workup.ADDITIONethylmagnesium bromide (1.0 ml of a 3.0M solution in diethyl ether, 3.0 mmol) was added
3. 3
   workup.ADDITIONAfter the addition
4. 4
   온도the reaction mixture was warmed to 0° C.
5. 5
   workup.STIRRINGstirred for one hour
6. 6
   기타The reaction was quenched
7. 7
   workup.ADDITIONby pouring slowly into a well-stirred ice-cold mixture of ethanol (40 ml) and concentrated HCl (5 ml)
8. 8
   기타The solvents were removed in vacuo
9. 9
   추출extracted with dichloromethane (4×20 ml)
10. 10
    건조The combined extracts were dried (Na2SO4)
11. 11
    농축concentrated in vacuo
12. 12
    기타the resulting oil was purified by flash chromatography on silica gel eluting with 10% i-propanol in ethyl acetate

실험 절차

A solution of N-methoxy-N-methyl-3,3-bis(diethoxyphosphinyl)propionamide (1.00 g, 2.6 mmol) in THF (5 ml) was slowly added to a slurry of 80% sodium hydride (80 mg, 2.7 mmol) in THF (10 ml) at 0° C. Stirring was continued until all of the hydride was consumed (~20 minutes). The solution was cooled to -78° C. and ethylmagnesium bromide (1.0 ml of a 3.0M solution in diethyl ether, 3.0 mmol) was added. After the addition, the reaction mixture was warmed to 0° C. and stirred for one hour. The reaction was quenched by pouring slowly into a well-stirred ice-cold mixture of ethanol (40 ml) and concentrated HCl (5 ml). The solvents were removed in vacuo, the residue was taken up in brine (20 ml) and extracted with dichloromethane (4×20 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo, and the resulting oil was purified by flash chromatography on silica gel eluting with 10% i-propanol in ethyl acetate to give the title compound (0.50 g, 54%) as a pale yellow oil.

출처