تفاعل #2066

معادلة التفاعل

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

sodium hydride

THF

THF

hydride

→

title compound

المردود 54.0%

tetraethyl 3-oxopentane-1,1-bisphosphonate

المردود 54.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىwas 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
   درجة الحرارةthe reaction mixture was warmed to 0° C.
5. 5
   workup.STIRRINGstirred for one hour
6. 6
   أخرىThe 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
   أخرىThe solvents were removed in vacuo
9. 9
   استخلاصextracted with dichloromethane (4×20 ml)
10. 10
    تجفيفThe combined extracts were dried (Na2SO4)
11. 11
    تركيزconcentrated in vacuo
12. 12
    أخرىthe resulting oil was purified by flash chromatography on silica gel eluting with 10% i-propanol in ethyl acetate

الإجراء التجريبي

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.

المصدر