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Volumn , Issue 20, 2008, Pages 3121-3124

Synthesis of O,O-diethyl arylthiophosphonate from O-aryl-O,O- diethylthiophosphate

Author keywords

Metallation; Phenols; Phosphorylation; Rearrangement

Indexed keywords

EID: 58149331412 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1087362 Document Type: Article

Times cited : (8)

References (20)

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19
- 58149347953
- Preparation of Thiophosphates 1a-i Represented by the Preparation of O,O-Diethyl 6-Bromo-2-(diethoxythiophosphinyl)-4- methylphenylthiophosphonate (1g, A solution of the phenolic derivative 2c (3.70 g, 8.85 mmol, triethylamine (1.48 mL, 10.6 mmol, 1.2 equiv) and DMAP (0.108 g, 0.88 mmol, 0.1 equiv) in THF (36 mL) was slowly added (15 min) to a solution of O,O-diethylchlorothiophosphate (1.67 g, 8.85 mmol) in THF (10 mL, The solution was then stirred overnight. The obtained suspension was filtered on celite and washed with Et2O. The filtrate was concentrated and redissolved in Et2O (80 mL, The organic phase was washed with H2O (2 x 20 mL) and brine (15 mL, dried over MgSO 4, filtered and concentrated. The obtained crude product was purified by column chromatography over silica gel (70-230 mesh; pentane-EtOAc, 100:5) to produce 1g (87% yield) as a colorless solid; mp 81°C. 1H NMR
- 2: C, 36.67; H, 5.13; S, 13.05. Found: C, 36.74; H, 5.10; S, 13.02.

20
- 58149357826
- Synthesis of Thiophosphonate 2-2i from Thiophosphate Represented by the Preparation of O,O-Diethyl 6-Hydroxy-2- pyridinylthiophosphonate(2f, n-Butyllithium (1.5 M in n-hexane, 2.25 mL, 3.38 mmol, 1.1 equiv) was added dropwise to a solution of 1f (1 g, 3.07 mmol) in THF (10 mL) previously cooled to -78°C. At the end of the addition, the solution was left to warm slowly. Then an aqueous solution of ammonium chloride was added (10 mL, The aqueous phase was extracted with Et2O (3 x 30 mL, The combined organic phases were washed with H2O and dried over MgSO4. After filtration and concentration the crude product was purified by column chromatography over silica gel (PE-EtOAc, 5:1) to produce the pure compound 2f as a white solid in 85% yield; mp 70°C. 1H NMR (300 MHz, CDCl3, δ, 1.37 t, 3JHH, 7.0 Hz, 6 H, OCH 2CH3
- -1.

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