3-Phenylphenol → HCID 9862294, compound

HRID 2120231Notes

Reaction equation

HRID 2120231 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][C:38](=[O:44])[NH:39]2.[C:45]1([C:51]2[CH:52]=[C:53](O)[CH:54]=[CH:55][CH:56]=2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O1CCCC1>[C:45]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:50]=[CH:49][CH:48]=[C:47]([O:32][CH2:33][CH2:34][C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][C:38](=[O:44])[NH:39]3)[CH:46]=1

Participants

6

Reactant 4

HCID 113813-PhenylphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9862294HCID 9862294, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.58 mL, 10 mmol) was added to a solution of triphenylphosphine (2.62 g, 10 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.77 g, 10 mmol) followed by 3-phenylphenol (1.7 g, 10 mmol). The mixture was stirred at room temperature for one day and the solvent was evaporated. The residue was dissolved in ethyl acetate (150 mL) and the organic solvent was washed with 2 N hydrochloric acid (3×50 mL), saturated sodium bicarbonate solution and brine. The residue was chromatographed on silica gel eluting with ethyl acetate: hexane 2:8 to give 1.19 g (36%) of 4-[2-(biphenyl-3-yloxy)-ethyl]-1,3-dihydro-indol-2-one.

Workup

  1. stirringThe mixture was stirred at room temperature for one day
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  4. washthe organic solvent was washed with 2 N hydrochloric acid (3×50 mL), saturated sodium bicarbonate solution and brine
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate: hexane 2:8

Sources & evidence

ORD record
ord-f94554501e4d453dbd33f5392edf2827
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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