Triethylamine → Ethyl 3-phenylpropyl 3-trifluoromethylbenzylphosphonate

HRID 1733815Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:6])[OH:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[C:24]1([CH2:30][CH2:31][CH2:32]O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.FC(F)(F)C1C=C(C=CC=1)CP(=O)(OCC)OCl.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[F:16][C:14]([F:17])([F:15])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][P:4](=[O:5])([O:6][CH2:32][CH2:31][CH2:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:3][CH2:1][CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-trifluoromethylbenzylphosphonic acid mono ethyl ester (1.5 g, 5.6 mmol) was dissolved in 20 mL of CH2Cl2 and cooled to 0° C. under nitrogen. After the oxalyl chloride (8.46 mmol) had been added, 0.04 mL of DMF was slowly added in 3 portions, and the resultant mixture was stirred at room temperature for 3 hours. Evaporation in vacuo gave the crude acid chloride which was used without further purification. 3-Phenyl-1-propanol (0.76 g, 5.6 mmol), in 15 mL of CH2Cl2, was added to a cold mixture of crude chloro ethyl 3-trifluoromethylbenzylphosphonate (5.6 mmol), triethylamine (0.85 g, 8.4 mmol), and CH2Cl2 (20 mL) cooled at 0° C. The resultant reaction mixture was allowed to stir at room temperature for 4 hours. Evaporation of the volatile components gave a quantitative yield of the expected product. Purification by column chromatography (silica gel, 25% ethyl acetate/hexane) gave 1.66 g (52.3%) of analytically pure product as a pale yellow oil. D.C.I.M.S.[MH+, 387].

Workup

customEvaporation in vacuo
customgave the crude acid chloride which
customwas used without further purification
temperaturecooled at 0° C
customThe resultant reaction mixture
customEvaporation of the volatile components

Sources & evidence

ORD record: ord-d97bde0ff6984d6098563f62932b87b0
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05532226

Reaction notes

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