تفاعل #57047

معادلة التفاعل

dimethyl methylphosphonate

n-BuLi

Methyl 3-chlorophenylacetate

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product

المردود 26.0%

Dimethyl 3-(3-chlorophenyl)-2-oxopropylphosphonate

المردود 26.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred for 2 hours at −78° C.
2. 2
   أخرىThe mixture was quenched with addition of 1N HCl to pH 4-5
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with brine
5. 5
   تجفيفdried over MgSO4
6. 6
   أخرىThe residue was purified through flash chromatography on silica gel (MeOH/CH2Cl2 1.5/98.5)

الإجراء التجريبي

To a solution of dimethyl methylphosphonate (4.32 mL, 40 mmol) in anhydrous THF (40 mL), cooled at −78° C. was added n-BuLi (1.6 M in hexane, 27.5 mL, 44 mmol). The mixture was stirred for 30 minutes at this temperature under nitrogen. Methyl 3-chlorophenylacetate (3.69 mL, 20 mmol) was added dropwise for 10 minutes. The mixture was stirred for 2 hours at −78° C., gradually was warm to room temperature. The mixture was quenched with addition of 1N HCl to pH 4-5. The organic layer was separated, washed with brine and dried over MgSO4. The residue was purified through flash chromatography on silica gel (MeOH/CH2Cl2 1.5/98.5) to give the product (1.43 g) with colorless oil in 26% yield. 1H-NMR (CDCl3) δ 3.07 (d, J=21 Hz, 2H), 3.750 (s, 3H), 3.775 (s, 3H), 3.873 (s, 2H), 7.01 (t, J=8.0 Hz, 1H), 7.19 (s, 1H), 7.28 (d, J=8.0 Hz, 2H).

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