Tetrahydrofuran → HCID 86591629, 화합물

HRID 495460노트

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HRID 495460 반응식
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[N+:19]([C:22]1[C:29](OC)=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][C:23]=1[CH:24]=O)([O-:21])=[O:20].[NH4+].[Cl-].C1C[O:39][CH2:38]C1>O>[CH2:4]([O:5][C:6](=[O:7])[CH:8]=[CH:9][CH:10]=[CH:24][C:23]1[CH:26]=[C:27]([O:39][CH3:38])[C:28]([O:32][CH3:33])=[CH:29][C:22]=1[N+:19]([O-:21])=[O:20])[CH3:3]

참가 물질

7

반응물 5

HCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1524373,4-Dimethoxy-2-nitrobenzaldehydeHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

생성물 1

HCID 86591629HCID 86591629, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a suspension of NaH (0.24 g, 6.0 mmol) in THF (30 mL) at 0° C. was added a solution of triethyl 4-phosphonocrotonate (1.0 g, 4.0 mmol) in THF (5 mL) dropwise. The solution was warmed to RT and stirred for 1 h. Nitroveratraldehyde (0.844 g, 4.0 mmol) was added to the mixture in one portion and the reaction was stirred for an additional 30 min at RT. NH4Cl (aq., sat., 3 mL) was added slowly to quench the reaction, followed by H2O (30 mL). The THF solvent was removed under reduced pressure and the resulting mixture was extracted with EtOAc (3×10 mL). The organic extracts were combined, washed with brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the mixture was purified by chromatography on silica gel to afford the title compound.

후처리

  1. stirringthe reaction was stirred for an additional 30 min at RT
  2. customto quench
  3. customthe reaction
  4. customThe THF solvent was removed under reduced pressure
  5. extractionthe resulting mixture was extracted with EtOAc (3×10 mL)
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe mixture was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-e4c766c5234f499c9a39221c5686675d
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939874B2

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