反応 #57055

反応方程式

dimethyl methylphosphonate

n-BuLi

Methyl phenylacetate

→

product

収率 62.0%

Dimethyl 2-oxo-3-phenylpropylphosphonate

収率 62.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred for 2 hours at −78° C.
2. 2
   その他The mixture was quenched with addition of 1N HCl to pH 4-5
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with brine
5. 5
   乾燥dried over MgSO4
6. 6
   その他The residue was purified through flash chromatography on silica gel (MeOH: CH2Cl2=2:98)

実験手順

To a solution of dimethyl methylphosphonate (2.16 mL, 20 mmol) in anhydrous THF (30 mL), cooled at −78° C. was added n-BuLi (1.6 M in hexane, 13.75 mL, 22 mmol). The mixture was stirred for 30 minutes at this temperature under nitrogen. Methyl phenylacetate (1.40 mL, 10 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=2:98) to give the product (1.50 g) with colorless oil in 62% yield. 1HNMR (CDCl3, ppm) δ 3.074 (d, J=21 Hz, 2H), 3.760 (s, 3H), 3.762 (s, 3H), 3.86 (s, 2H), 7.31 (m, 5H).

出典