Triphenylphosphine → N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide

HRID 73972

반응식

HRID 73972 반응식
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.C(NC1C=C(OC(=O)C)C=CC=1)=O.[CH3:25][C:26](=[CH2:30])[CH2:27][CH2:28]O.CCOC(/N=N/C(OCC)=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1C=CC=CC=1.O>[CH3:30][C:26](=[CH2:25])[CH2:27][CH2:28][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 11776TriphenylphosphineHCID 121243-HydroxyacetanilideHCID 129883-Methyl-3-buten-1-olHCID 5462977Diethyl azodicarboxylateHCID 57470213Acetic acid 3-formylamino-phenyl ester

생성물 1

HCID 57567384N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide수율 52%

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

A suspension of the mixture of N-(3-hydroxy-phenyl)-acetamide and acetic acid 3-formylamino-phenyl ester (18.12 g, 0.12 mol), 3-methyl-but-3-en-1-ol (8.6 g, 0.1 mol), DEAD (87 g, 0.2 mol) and Ph3P (31.44 g, 0.12 mol) in benzene (250 mL) was heated at reflux overnight and then cooled to room temperature. The reaction mixture was poured into water and the organic layer was separated. The aqueous phase was extracted with EtOAc (300×3 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide (11 g, 52%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe organic layer was separated
  4. extractionThe aqueous phase was extracted with EtOAc (300×3 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-e10579a39eec48f0b3a2326d7aaaf826
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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