Sodium Carbonate → [2-(Methoxy)-3-nitrophenyl]acetaldehyde

HRID 15863

반응식

HRID 15863 반응식
COC1C([N+]([O-])=O)=CC=CC=1C=O.C1OCCOCCOCCOCCOCCOC1.[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:61][O:62][C:63]1[C:68]([N+:69]([O-:71])=[O:70])=[CH:67][CH:66]=[CH:65][C:64]=1/[CH:72]=[CH:73]/[O:74]C.COC1C([N+]([O-])=O)=CC=CC=1/C=C\OC.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.Cl>[CH3:61][O:62][C:63]1[C:68]([N+:69]([O-:71])=[O:70])=[CH:67][CH:66]=[CH:65][C:64]=1[CH2:72][CH:73]=[O:74]

참가 물질

10

반응물 7

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 140810742-Methoxy-3-nitrobenzaldehydeHCID 574542632-(methoxy)-1-[(E)-2-(methoxy)ethenyl]-3-nitrobenzeneHCID 684276382-(methyloxy)-1-[(Z)-2-(methyloxy)ethenyl]-3-nitrobenzene

생성물 1

HCID 57444344[2-(Methoxy)-3-nitrophenyl]acetaldehyde수율 54%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 2-(methoxy)-3-nitrobenzaldehyde in THF were added 18-Crown-6 (0.2 eq), (methoxymethyl)triphenylphosphonium chloride (2 eq) and potassium carbonate (6.5 eq). The resulting suspension was warmed to 60° C. for 2 hours then cooled to room temperature and filtered. The filtrate was concentrated under vacuum and purified by chromatography on a silica cartridge (eluent cyclohexane-ethyl acetate, 9:1) to give a mixture of 2-(methoxy)-1-[(E)-2-(methoxy)ethenyl]-3-nitrobenzene and 2-(methyloxy)-1-[(Z)-2-(methyloxy)ethenyl]-3-nitrobenzene. The alkene mixture was dissolved in THF and 6N hydrochloric acid (1:1), and stirred for 1 hour. The solution was made basic with aqueous sodium carbonate solution and extracted with DCM. The organic layer was washed (water, brine), dried (sodium sulfate) and concentrated under vacuum to give the title compound (54% overall yield).

후처리

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. custompurified by chromatography on a silica cartridge (eluent cyclohexane-ethyl acetate, 9:1)
  5. customto give
  6. extractionextracted with DCM
  7. washThe organic layer was washed (water, brine)
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-ecd9381d4e544e7cbe61b573e5005ff4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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