Hydrochloric Acid → 2,5-Diphosphonotetrahydrofuran

HRID 1165738Notes

Reaction equation

HRID 1165738 reaction equation
[P:1]([O:10]C(C)C)([O:6]C(C)C)[O:2]C(C)C.[P:14]([CH:18]1[CH2:22][CH2:21][CH:20](Br)[O:19]1)([OH:17])([OH:16])=[O:15].Cl>>[P:14]([CH:18]1[CH2:22][CH2:21][CH:20]([P:1]([OH:2])([OH:6])=[O:10])[O:19]1)([OH:17])([OH:16])=[O:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8304Triisopropyl phosphiteHCID 19860800HCID 19860800, compound

Product 1

HCID 148175552,5-Diphosphonotetrahydrofuran

Conditions

Temperature
170 °C

Procedure

Triisopropyl phosphite (0.33 ml, 1.2 mmol) was added to the 2-phosphono-5-bromotetrahydrofuran prepared in accordance with the process of Example II. The mixture was heated over a period of one half hour under a nitrogen atmosphere to 170° C. It was held at this temperature for two and one quarter hours and then cooled to room temperature. Concentrated hydrochloric acid (15 ml) was added and the resulting mixture was heated to reflux for five hours. The volatile components were removed under vacuum leaving 2,5-diphosphonotetrahydrofuran ("DPTHF") containing phosphorous acid as an impurity. The identity of the 2,5-diphosphonotetrahydrofuran was established by nuclear magnetic resonance spectroscopy (proton, phosphorus and carbon-13) and fast atom bombardment mass spectroscopy

Workup

  1. customprepared in accordance with the process of Example II
  2. waitIt was held at this temperature for two and one quarter hours
  3. temperaturecooled to room temperature
  4. temperaturethe resulting mixture was heated
  5. temperatureto reflux for five hours
  6. customThe volatile components were removed under vacuum

Sources & evidence

ORD record
ord-3006e1a3ec5947feb8976e628a6791b7
Source dataset
uspto-grants-1990_03
Patent number
US04911887

Reaction notes

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