Sodium Carbonate → trans-3'-[N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methylaminomethyl]propiophenone

HRID 1356800노트

반응식

HRID 1356800 반응식
[CH3:1][C:2]([CH3:11])([CH3:10])[C:3]#[C:4][CH:5]=[CH:6][CH2:7][NH:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:19][C:20]1[CH:21]=[C:22]([C:26](=[O:29])[CH2:27][CH3:28])[CH:23]=[CH:24][CH:25]=1>CN(C)C=O>[CH3:1][C:2]([CH3:11])([CH3:10])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:19][C:20]1[CH:21]=[C:22]([C:26](=[O:29])[CH2:27][CH3:28])[CH:23]=[CH:24][CH:25]=1)[CH3:9]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 185094641-(3-(Bromomethyl)phenyl)propan-1-oneHCID 53427009N,6,6-trimethylhept-2-en-4-yn-1-amine

생성물 1

HCID 18509386trans-3'-[N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methylaminomethyl]propiophenone수율 26.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

N-(6,6-dimethyl-2-hepten-4-ynyl)methylamine (trans:cis=about 3:1) (0.80 g; 5.29 mmol) and sodium carbonate (0.80 g; 7.56 mmol) were added to N,N-dimethylformamide (20 ml). While the mixture was stirred at room temperature, 3′-bromomethylpropiophenone (1.14 g; 5.04 mmol) in N,N-dimethylformamide (10 ml) was added dropwise. The mixture was stirred for 2.5 hours at room temperature, and poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.40 g of the target compound as orange oily matter (yield: 26.7%).

후처리

  1. stirringThe mixture was stirred for 2.5 hours at room temperature
  2. additionpoured into ice+saturated aqueous sodium bicarbonate solution
  3. extractionfollowed by extraction with ethyl acetate (100 ml)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-6619edbf38754e2fa2acbdc47bd1766d
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586633B1

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