Carbon Dioxide → HCID 59317564, compound

HRID 1008758Notes

Reaction equation

HRID 1008758 reaction equation
[C:1](=O)([O-])[NH2:2].[Li+].C(=O)=O.[Li][C:10](C)(C)[CH3:11].C[C:15]1([CH3:23])[C:19](=O)[C:18]#[C:17][C:16]1([CH3:22])C.Cl.[C:25](=O)([O-])O.[Na+].[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1.C(OCC)(=O)C.CCCCCC.CC(C)=O.C(OCC)C>[CH3:22][C:16]1[C:15]([CH3:23])=[C:19]([CH3:25])[CH:18]([CH3:17])[C:36]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:31]=1[NH:2][CH2:1][CH2:11][CH2:10]2

Participants

13

Reactant 7

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 1140TolueneHCID 516892Sodium BicarbonateHCID 23703745Lithium carbamateHCID 121433819HCID 121433819, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59317564HCID 59317564, compoundYield 40%

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

The prepared lithium carbamate compound (8.47 g, 42.60 mmol) was put in the Schlenk flask. Tetrahydrofuran (4.6 g, 63.9 mmol) and 45 mL of diethyl ether were sequentially added. After the flask was put in a low temperature bath having the temperature of −20° C. which included acetone and a small amount of dry ice and then agitated for 30 min, tert-BuLi (25.1 mL, 1.7M, 42.60 mmol) were added thereto. At this time, the color of the resulting substance was changed to the red color. While the temperature was maintained at −20° C., the agitation was performed for 6 hours. The CeCl3.2LiCl solution (129 mL, 0.33M, 42.60 mmol) and tetramethylcyclopentinone (5.89 g, 42.60 mmol) which were dissolved in tetrahydrofuran were mixed with each other in the syringe, and then added to the flask in a nitrogen atmosphere. The temperature was slowly increased to normal temperature. After 1 hour, the thermostat was removed to increase the temperature to normal temperature. After water (15 mL) was added, ethyl acetate was added and then filtered to obtain a filtrate solution. The filtrate solution was transported to the separatory funnel and a hydrochloric acid (2N, 80 mL) was added and then shaken for 12 min. Additionally, the saturated sodium hydrogen carbonate aqueous solution (160 mL) was added to perform neutralization, and the organic layer was extracted. Anhydrous magnesium sulfate was added to the organic layer to remove water and perform the filtration, the filtrate solution was taken, and the solvent was removed. The yellow oil was obtained by using a column chromatography. Hexane:toluene (v/v, 10:1). Hexane:ethyl acetate (v/v, 10:1). The yield was 40%.

Workup

  1. customAfter the flask was put in a low temperature bath
  2. customthe temperature of −20° C. which
  3. additionwere mixed with each other in the syringe
  4. additionadded to the flask in a nitrogen atmosphere
  5. temperatureThe temperature was slowly increased to normal temperature
  6. waitAfter 1 hour
  7. customthe thermostat was removed
  8. temperatureto increase the temperature to normal temperature
  9. additionAfter water (15 mL) was added
  10. additionethyl acetate was added
  11. filtrationfiltered
  12. customto obtain a filtrate solution
  13. extractionthe organic layer was extracted
  14. additionAnhydrous magnesium sulfate was added to the organic layer
  15. customto remove water
  16. filtrationthe filtration
  17. customthe solvent was removed
  18. customThe yellow oil was obtained

Sources & evidence

ORD record
ord-74aa4119efc843d9aa4899be30ead42b
Source dataset
uspto-grants-2011_07
Patent number
US07972987B2

Reaction notes

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