Acetic Acid → HCID 20313165, compound

HRID 839721Notes

Reaction equation

C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[C:13]1([CH:19]2[CH2:22][CH:21]([C:23](OC)=[O:24])[CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>CCCCCC.O1CCCC1>[O:24]=[C:23]([CH:21]1[CH2:22][CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20]1)[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyl-lithium (16.0ml. of a 1.43M solution in hexane) was added dropwise to a stirred solution of dimethyl methylphosphonate (2.86g.) in dry tetrahydrofuran (25ml.) at -78° C. in an atmosphere of argon. After 10 minutes, a solution of the methyl 3-phenylcyclobutanecarboxylate mixture (2.18g.) in dry tetrahydrofuran (25ml.) was added, and stirred at -78° C. for 2 hours. The reaction mixture was then neutralized by the addition of glacial acetic acid, warmed to room temperature and the tetrahydrofuran was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate extract was dried over magnesium sulphate and evaporated under reduced pressure, to give dimethyl 2-oxo-2-(3-phenylcyclobutyl)-ethylphosphonate, as a mixture of cis and trans isomers. The n.m.r. spectrum in deuteriochloroform showed the following characteristic features (δ values):-

Workup

temperaturewarmed to room temperature
customthe tetrahydrofuran was evaporated under reduced pressure
customThe residue was partitioned between ethyl acetate and water
extractionThe ethyl acetate extract
dry with materialwas dried over magnesium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-f8bce1c61a21475ca54f18dacb38ba16
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04096337

Reaction notes

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