Triphenylphosphine → HCID 18626516, 화합물

HRID 368346

반응식

HRID 368346 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.[N:13]1([CH2:18][CH2:19]O)[CH:17]=[CH:16][N:15]=[CH:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O>[N:13]1([CH2:18][CH2:19][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:12])[CH2:7][CH2:8][NH:9]3)=[CH:4][CH:3]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 74168N-(2-Hydroxyethyl)imidazoleHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18626484HCID 18626484, 화합물

생성물 1

HCID 18626516HCID 18626516, 화합물수율 11.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Under N2, a solution of 0.8 g (5.0 mmol) of 7-hydroxy-1,2,3,4-tetrahydro-4-quinolinone in 20 mL of THF was treated with 0.62 g (5.5 mmol) of 2-(1H-1-imidazolyl)-1-ethanol and 1.13 (5.0 mmol) of tripenylphosphine. The mixture was warmed to effect solution, then allowed to cool to room temperature. This was then treated over 10 minutes with 0.8 mL (5.0 mmol) of diethyl azodicarboxylate. Some solid formed and the mixture was allowed to stir at room temperature for 3 days. The mixture was diluted with EtOAc and filtered. The filtrate was washed twice with H2O, saturated NaHCO3, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with CHCl3 /MeOH (90/10), gave 150 mg (11.8% yield) of the product as a golden oil. The structure was confirmed by mass spectroscopy. MS m/z 258 (M+H+).

후처리

  1. temperatureThe mixture was warmed
  2. customSome solid formed
  3. filtrationfiltered
  4. washThe filtrate was washed twice with H2O, saturated NaHCO3
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product
  7. washChromatography on silica gel, eluting with CHCl3 /MeOH (90/10)

출처 및 근거

ORD 기록
ord-1e7b4f82414246c5807297b1103098d7
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133303

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