Carbon Dioxide → HCID 54305009, compound

HRID 1248547Notes

Reaction equation

HRID 1248547 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([P:24](=[O:33])([O:29][CH:30]([CH3:32])[CH3:31])[O:25][CH:26]([CH3:28])[CH3:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[C:34](=[O:36])=[O:35]>CCOCC.C1COCC1>[CH:30]([O:29][P:24]([CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:34]([OH:36])=[O:35])([O:25][CH:26]([CH3:28])[CH3:27])=[O:33])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 20276894HCID 20276894, compoundHCID 178418339Butyllithium

Product 1

HCID 54305009HCID 54305009, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

196 g (1.94 moles) of diisopropylamine was added to a flame-dried, 5 liter flask fitted with mechanical stirrer, condenser, thermometer and addition funnel. The flask was cooled to 0°-10° C. using a dry ice/acetone bath. 808 ml of n-butyllithium (2.4M, 1.95 moles) was slowly added, while the flask was kept at 0°-10° C. The solution was stirred for an additional 15 minutes and then chilled to -78° C. 598 g (1.84 moles) of diisopropyl undecylphosphonate was added in 1000 ml of freshly distilled THF. (The addition rate should be slow enough to maintain the temperature below -60° C.) The mixture was stirred for an additional 2 hours and then poured carefully into a 12 liter flask containing about 2 kg of dry ice in 3.78 liters of ether. This mixture was allowed to stand and warm slowly overnight. The solution was extracted with water to collect the lithium salt of the product. The organic layers contained any unreacted diisopropyl undecylphosphonate. The water layer was acidified to pH 2.0 using concentrated HCl and extracted with 500 ml of ether three times. The combined ether extracts were dried over magnesium sulfate, filtered, and flash evaporated. The product was a viscous oil weighing 553 g (81% yield) and was sufficiently pure (by 1H NMR) for use in the next step.

Workup

  1. customfitted with mechanical stirrer, condenser
  2. additionthermometer and addition funnel
  3. temperatureThe flask was cooled to 0°-10° C.
  4. customwas kept at 0°-10° C
  5. temperatureto maintain the temperature below -60° C.) The mixture
  6. stirringwas stirred for an additional 2 hours
  7. additionpoured carefully into a 12 liter flask
  8. temperaturewarm slowly overnight
  9. extractionThe solution was extracted with water
  10. customto collect the lithium salt of the product
  11. extractionextracted with 500 ml of ether three times
  12. dry with materialThe combined ether extracts were dried over magnesium sulfate
  13. filtrationfiltered
  14. customflash evaporated

Sources & evidence

ORD record
ord-c3b990a24ef041549a1efeaf10828c8c
Source dataset
uspto-grants-1985_06
Patent number
US04525289

Reaction notes

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