Methyl vinyl ketone → Diethyl (3-oxobutyl)phosphonate
Reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[O-]CC.[Na+].[Na].[CH:14]([C:16]([CH3:18])=[O:17])=[CH2:15]>C(O)C.C(Cl)(Cl)Cl>[O:17]=[C:16]([CH3:18])[CH2:14][CH2:15][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 15 °C
Procedure
To 243 grams (1.76 moles) of diethyl phosphite stirred under nitrogen and protected by a drying tube was added a solution of sodium ethoxide prepared from 5.07 grams (0.22 mole) of sodium in 100 ml of anhydrous ethanol. Methyl vinyl ketone, 112 grams (1.60 moles), was then added at such a rate as to keep the temperature at 35°-40° C. The addition required about one hour. The reaction mixture was stirred for one-half hour after the addition was completed and was stripped to dryness in vacuo at 60° C/16 mm. The residue was taken up in 600 ml of chloroform, and the solution cooled to 15° C and washed successively with dilute acid, water and saturated sodium chloride solution. After drying, the chloroform solution was distilled to yield 112 grams of diethyl 3-oxobutylphosphonate as a colorless liquid, B.P. 106° C/0.05 mm, nD 25 1.4340. VPC indicated that the product was 90% pure.
Workup
- customprotected by a drying tube
- customat 35°-40° C
- additionThe addition required about one hour
- additionafter the addition
- customwas stripped to dryness in vacuo at 60° C
- washwashed successively
- additionwith dilute acid, water and saturated sodium chloride solution
- customAfter drying
- distillationthe chloroform solution was distilled
Sources & evidence
- ORD record
- ord-c09dce7f8cdb44148b092b5eec8062b4
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04093809
Reaction notes
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