反应 #2066

反应方程式

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

sodium hydride

THF

THF

hydride

→

title compound

收率 54.0%

tetraethyl 3-oxopentane-1,1-bisphosphonate

收率 54.0%

反应条件

后处理

1. 1
   其他was 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
   温度the reaction mixture was warmed to 0° C.
5. 5
   workup.STIRRINGstirred for one hour
6. 6
   其他The 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
   其他The solvents were removed in vacuo
9. 9
   萃取extracted with dichloromethane (4×20 ml)
10. 10
    干燥The combined extracts were dried (Na2SO4)
11. 11
    浓缩concentrated in vacuo
12. 12
    其他the resulting oil was purified by flash chromatography on silica gel eluting with 10% i-propanol in ethyl acetate

实验过程

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.

来源