Triethyl phosphite → Phosphonic acid, [(5-phenyl-3-isoxazolyl)methyl]-, diethyl ester

HRID 1194064Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.[CH2:14]([O:16][P:17]([O:21]CC)[O:18][CH2:19][CH3:20])[CH3:15]>>[CH2:14]([O:16][P:17]([CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1)([O:18][CH2:19][CH3:20])=[O:21])[CH3:15]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 14847693-(Chloromethyl)-5-phenyl-1,2-oxazole

Product 1

HCID 10935300Phosphonic acid, [(5-phenyl-3-isoxazolyl)methyl]-, diethyl esterYield 63%

Procedure

3-Chloromethyl-5-phenylisoxazole (2.07 g, 10 mmol) and triethylphosphite (1.72 ml, 10 mmol) were heated at reflux for 2 h then the mixture distilled under reduced pressure to yield the title compound (1.85 g, 6.27 mmol, 63%); b.p. 192° at 0.5 mm Hg; νmax (film) 2980, 2900, 1610, 1590, 1570, 1500, 1450, 1420, 1390, 1250, 1160, 1060-1010, 970, 760, 690 cm-1 ; δH (CDCl3) 1.30 (3H, t, J 7 Hz, OCH2CH3), 3.30 (2H, d, J 21 Hz, CH2 --P), 4.20 (2H, m, OCH2CH3), 6.60 (1H, s, CH-het), 7.2-7.9 (5H, m, Ph).

Workup

temperatureat reflux for 2 h
distillationthe mixture distilled under reduced pressure

Sources & evidence

ORD record: ord-b2a8e616a00044b891a13e3607d4bfb1
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812470

Reaction notes

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