Carbon Dioxide → 4-(Diethylamino)but-2-ynoic acid

HRID 1068978Notes

Reaction equation

HRID 1068978 reaction equation
C([Li])CCC.[CH2:6]([N:8]([CH2:12][CH3:13])[CH2:9][C:10]#[CH:11])[CH3:7].[C:14](=[O:16])=[O:15].O>CCCCCC.O1CCCC1.CO>[CH2:6]([N:8]([CH2:12][CH3:13])[CH2:9][C:10]#[C:11][C:14]([OH:16])=[O:15])[CH3:7]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 20010DietylaminopropinHCID 178418339Butyllithium

Product 1

HCID 224666854-(Diethylamino)but-2-ynoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium in hexane (54 mL, 2.5M in n-hexane) was slowly added to 1-diethylamino-2-propyne (15 g, 135 mmol) in 60 mL of tetrahydrofuran under nitrogen. The mixture was stirred for 1 hr at −78° C., then dry carbon dioxide was passed through 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 9.2 g of 4-diethylamino-but-2-ynoic acid: mass spectrum (m/e):M+H 156.

Workup

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

Sources & evidence

ORD record
ord-dd423e418b2044898e38286039b25778
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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