Iodine → Diethyl 5-iodo-2-furanphosphonate

HRID 2222105Notes

Reaction equation

HRID 2222105 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[P:6]([O:11][CH2:12][CH3:13])(=[O:10])[O:7][CH2:8][CH3:9].C([N-]C1CCCCC1)(C)C.[Li+].[I:25]I>C1COCC1>[I:25][C:5]1[O:1][C:2]([P:6]([O:7][CH2:8][CH3:9])(=[O:10])[O:11][CH2:12][CH3:13])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 807IodineHCID 10877271Lithium cyclohexylisopropylamideHCID 12485182Phosphonic acid, 2-furanyl-, diethyl ester

Product 1

HCID 22280644Diethyl 5-iodo-2-furanphosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of diethyl 2-furanphosphonate (prepared as described in Step A, Example 1) (1 mmol) in 2 mL THF was cooled to −78° C. and added to a solution of lithium isopropylcyclohexylamide (LICA) (1 mmol) in 2 mL THF at −78° C. over 20 min. The resulting mixture was stirred −78° C. for 20 min and added into a solution of iodine (1 mmole) in 1 mL TIF at −78° C. over 20 min. The mixture was then stirred at −78° C. for 20 min. Extraction and chromatography provided diethyl 5-iodo-2-furanphosphonate as a yellow oil.

Workup

  1. stirringThe mixture was then stirred at −78° C. for 20 min
  2. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-dac36a9d6e5e4cdfa57bf148d08e3481
Source dataset
uspto-grants-2008_05
Patent number
US07371739B2

Reaction notes

Loading…