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

HRID 379148노트

반응식

HRID 379148 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 150797524-(Dimethylamino)but-2-ynoic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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 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.

후처리

  1. customthrough 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

출처 및 근거

ORD 기록
ord-33d35dca479141c7b0f23a4c828c0d0d
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297258B1

반응 노트

불러오는 중…