Diethyl chlorophosphate → HCID 88432937, compound

HRID 399721Notes

Reaction equation

HRID 399721 reaction equation
[CH3:1][CH:2]([CH3:10])[CH2:3][P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6].C([Li])(CC)C.[P:16](Cl)([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1>[CH3:6][O:5][P:4]([CH:3]([P:16](=[O:17])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[CH:2]([CH3:10])[CH3:1])(=[O:9])[O:7][CH3:8]

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 54458283HCID 54458283, compoundHCID 178418400CID 53628100

Product 1

HCID 88432937HCID 88432937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2--methylpropylphosphonic acid, dimethyl ester (2.20 g, 14.47 mmol) in anhydrous THF (200 ml) is added sec-butyllithium (20.04 ml, 26.05 mmol, 1.3M in cyclohexane) at 0° C. Following the addition, stirring is continued for an additional 30 minutes. This solution is then slowly added to a solution of diethyl chlorophosphate (2.50 9, 14.47 mmol) in anhydrous THF (100 ml) at room temperature. After stirring the reaction overnight, the mixture is quenched by the addition of a saturated aqueous solution of sodium bicarbonate and then extracted with methylene chloride. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography with 30% acetone in hexanes on silica gel.

Workup

  1. additionthe addition
  2. stirringAfter stirring
  3. customthe reaction overnight
  4. customthe mixture is quenched by the addition of a saturated aqueous solution of sodium bicarbonate
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product is purified by flash chromatography with 30% acetone in hexanes on silica gel

Sources & evidence

ORD record
ord-6cdbbb036886481eae1d23e95ea6106d
Source dataset
uspto-grants-1998_10
Patent number
US05824661

Reaction notes

Loading…