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

HRID 1727541Notes

Reaction equation

HRID 1727541 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13](=[CH2:17])[CH2:14][CH2:15]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>[CH3:17][C:13](=[CH2:12])[CH2:14][CH2:15][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 121243-HydroxyacetanilideHCID 129883-Methyl-3-buten-1-olHCID 5462977Diethyl azodicarboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A suspension of the mixture of N-(3-hydroxy-phenyl)-acetamide and acetic acid 3-fonnylamino-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%).

Workup

  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

Sources & evidence

ORD record
ord-3f1a310cc40343ffa10c61110354fc95
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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