Triphenylphosphine → HCID 9926167, compound

HRID 2120229Notes

Reaction equation

HRID 2120229 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.[CH:45]([C:48]1[CH:49]=[C:50](O)[CH:51]=[CH:52][CH:53]=1)([CH3:47])[CH3:46]>O1CCCC1>[CH:45]([C:48]1[CH:53]=[C:52]([CH:51]=[CH:50][CH:49]=1)[O: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)([CH3:47])[CH3:46]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 120593-IsopropylphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9926167HCID 9926167, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.47 mL, 3 mmol) was added to a solution of triphenylphosphine (0.786 g, 3 mmol) in tetrahydrofuran (10 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 (0.53 g, 3 mmol) (Hayler, J. D.; Howic, S. L. B.; Giles, R. G.; Negus, A.; Oxley, P. W.; et al; J. Heteocycl. Chem.; 32; 3; 1995; 875-882), followed by 3-isopropylphenol (0.41 mL, 3 mmol). The mixture was stirred at room temperature for one day and the solvent was evaporated. The residue was chromatographed on silica gel eluting with ethyl acetate: hexane 1:9 to give 120 mg (14%) of 4-[2-(3-isopropyl-phenoxy)-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. customThe residue was chromatographed on silica gel eluting with ethyl acetate: hexane 1:9

Sources & evidence

ORD record
ord-0143cdad58d642ed89ab3e2e94313f01
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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