Triphenylphosphine → HCID 15506060, compound

HRID 384128Notes

Reaction equation

HRID 384128 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=CC=C[CH:14]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(O)(C)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH:13]([CH3:18])[CH3:14])[CH:6]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 39129Methyl 3-HydroxyphenylacetateHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 15506060HCID 15506060, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl(3-hydroxyphenyl)acetate (200 mg) in tetrahydrofuran (5 ml), 0.15 ml of isopropyl alcohol, 480 mg of triphenylphosphine, and 0.82 ml of diethyl azodicarboxylate (45% toluene solution) were added, and the reaction solution was stirred overnight at room temperature. The reaction solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-60/40)) to afford the title compound as a colorless oil.

Workup

  1. distillationThe reaction solvent was distilled off under reduced pressure
  2. customthe residue obtained
  3. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-60/40))

Sources & evidence

ORD record
ord-e82c5e26b59446ea86708ccf0201dc1d
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

Loading…