Carbon Dioxide → HCID 15079752, compound

HRID 276819Notes

Reaction equation

HRID 276819 reaction equation
C([Li])CCC.[CH3:6][N:7]([CH3:11])[CH2:8][C:9]#[CH:10].[C:12](=[O:14])=[O:13].O>CCCCCC.O1CCCC1.CO>[CH3:6][N:7]([CH3:11])[CH2:8][C:9]#[C:10][C:12]([OH:14])=[O:13]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 81643N,N-DimethylpropargylamineHCID 178418339Butyllithium

Product 1

HCID 15079752HCID 15079752, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium in hexane (96 mL, 2.5 M in n-hexane) was slowly added to 1-dimethylamino-2-propyne (20 g, 240 mmol) in 100 mL of tetrahydrofuran under nitrogen. The mixture was stirred for 1 h at −78° C., then dry carbon dioxide was pass through the reaction overnight. The resulting solution was poured into water and washed with ethyl acetate. The aqueous layer was evaporated under reduced pressure to give the crude acid. The dry acid was dissolved in methanol, and the insoluble salt was removed via filtration. The filtrate was collected and dried in vacuo to give 15.6 g of 4-dimethylamino-but-2-ynoic acid: mass spectrum (m/e):M−H 126.

Workup

  1. customthrough the reaction overnight
  2. washwashed with ethyl acetate
  3. customThe aqueous layer was evaporated under reduced pressure
  4. customto give the crude acid
  5. customthe insoluble salt was removed via filtration
  6. customThe filtrate was collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-550a887d60f9488fbc9e51663994a57f
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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