Triphenylphosphine → HCID 68552474, compound

HRID 854500Notes

Reaction equation

HRID 854500 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-c7d7590e6dde4291b16935f100700ac7
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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