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

HRID 2373635노트

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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]

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온도: 60 °C

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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

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

출처 및 근거

ORD 기록: ord-7d441236c6a64d21a67769890c5a62dd
출처 데이터셋: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07459456B2

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생성물 1

시약·촉매·용매 2

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