Triphenylphosphine → 4-[2-[2-(3-chloropropoxy)-phenyl]-ethenyl]-1H-indol

HRID 1906191Notes

Reaction equation

HRID 1906191 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]=[CH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.N(C(OCC)=O)=NC(OCC)=O.[Cl:31][CH2:32][CH2:33][CH2:34]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:31][CH2:32][CH2:33][CH2:34][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]=[CH:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 123133-Chloro-1-propanol2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 541413862-[(1H-indol-4-yl)-ethenyl]-phenol

Product 1

HCID 541698344-[2-[2-(3-chloropropoxy)-phenyl]-ethenyl]-1H-indol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an inert atmosphere, 235 mg of 2-[(1H-indol-4-yl)-ethenyl]-phenol in 20 ml of tetrahydrofuran with 0.15 ml of diethyl azodicarboxylate, 0.1 ml of 3-chloro-1-propanol, and 262 mg of triphenylphospine were stirred for 5 hours. Then 0.1 ml of 3-chloro-1-propanol, 0.15 ml of diethyl azodicarboxylate and 262 mg of triphenyl phospine were added, and after 15 hours of stirring at ambient temperature, the mixture was concentrated to dryness. The residue was purified by chromatography on silica (eluent: benzene) to obtain 310 mg of 4-[2-[2-(3-chloropropoxy)-phenyl]-ethenyl]-1H-indol.

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. customThe residue was purified by chromatography on silica (eluent: benzene)

Sources & evidence

ORD record
ord-59cd1a96914343a58b06afbad75f1f1d
Source dataset
uspto-grants-1987_03
Patent number
US04650811

Reaction notes

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