Reaktion #57061

Reaktionsgleichung

methyl 1-butylcyclobutanecarboxylate

dimethyl methylphosphonate

n-BuLi

→

title compound

dimethyl 2-(1-butylcyclobutyl)-2-oxoethylphosphonate

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 30 minutes at −78° C.
2. 2
   Sonstigeto warn to room temperature
3. 3
   SonstigeThe reaction was quenched with 5% HCl
4. 4
   Extraktionextracted with CH2Cl2 (3×30 mL)
5. 5
   Waschenthe combined organic phase was washed with brine
6. 6
   Trocknendried (MgSO4)
7. 7
   EinengenAfter concentration, flash chromatography (silica gel, 1:1 ethylacetate:hexanes)

Vorschrift

To a solution of dimethyl methylphosphonate (1.46 g, 11.8 mmol) in anhydrous THF (25 mL) at −78° C. was added n-BuLi (7.4 mL, 1.6 M, 11.8 mmol) dropwise under Ar. The reaction was stirred for 15 minutes. A solution of methyl 1-butylcyclobutanecarboxylate (1.00 g, 5.87 mmol) in THF (5 mL) was added dropwise. The reaction mixture was stirred for 30 minutes at −78° C., after which it was allowed to warn to room temperature. The reaction was quenched with 5% HCl, extracted with CH2Cl2 (3×30 mL), the combined organic phase was washed with brine, dried (MgSO4). After concentration, flash chromatography (silica gel, 1:1 ethylacetate:hexanes), the title compound was obtained as a colorless oil. 1HNMR (CDCl3) δ 0.85˜0.89 (m, 3H), 1.05˜1.15 (m, 2H), 1.22˜1.35 (m, 2H), 1.65˜1.95 (m, 6H), 2.35˜2.50 (m, 2H), 3.00 (s, 1H0, 3.06 (s, 1H), 3.78 (s, 3H), 3.82 (s, 3H). MS (m/z) 285 (M+Na)

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