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

HRID 73972

反応式

HRID 73972 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e10579a39eec48f0b3a2326d7aaaf826
出典データセット
uspto-grants-2014_09
特許番号
US08829204B2

関連ノート

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