Triphenylphosphine → HCID 68552474, compound

HRID 2243163Notes

Reaction equation

HRID 2243163 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:30][C:31]1[CH:39]=[CH:38][C:34]([CH2:35][CH2:36]O)=[CH:33][CH:32]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:30][C:31]1[CH:39]=[CH:38][C:34]([CH2:35][CH2:36][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 160545-HydroxyindoleHCID 820684-Fluorophenethyl AlcoholHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 68552474HCID 68552474, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.06 g (8 mmol) 5-hydroxyindole and 2.09 g (8 mmol) triphenylphosphine in 40 ml anhydrous THF, cooled to 0° C. in ice, was added 1.0 mL (8 mmol) 4-fluorophenethylalcohol and 1.6 ml (8 mmol) diisopropylazodicarboxylate. The solution was allowed to gradually come to room temperature overnight. The solution was concentrated and the residue was chromatographed on silica using 20-25% EtOAc-hexane to afford 0.525 g 5-[2-(4-fluoro-phenyl)-ethoxy]-1H-indole as a white solid.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was chromatographed on silica using 20-25% EtOAc-hexane

Sources & evidence

ORD record
ord-f2f34edb049544dda08eec968136298f
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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