Indole → HCID 15677792, compound

HRID 2288876Notes

Reaction equation

HRID 2288876 reaction equation
OCCC1N[C:6]2[C:11](C=1)=[CH:10][C:9](CC(OC)=O)=[CH:8][CH:7]=2.[O:18]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27](CCC)[CH:26]=1)[C:19]1C=CC=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.N1C2C(=CC=CC=2)C=C1>C1COCC1>[CH2:19]([O:18][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:27][CH:26]=1)[CH:20]=[CH2:21]

Participants

7

Reactant 5

HCID 798IndoleHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 15462903Methyl 2-(2-hvdroxyethyl)indole-5-acetateHCID 154629044-Phenoxy-2-propylphenol

Product 1

HCID 15677792HCID 15677792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(2-hydroxyethyl)indole-5-acetate, from Example 1, Step E (7.6 g), 4-phenoxy-2-propylphenol (8.28 g), triphenylphosphine (11.2 g), DIAD (8.5 mL) and THF (125 mL) was stirred under nitrogen at room temperature. After stirring overnight none of the starting indole remained as determined by TLC and the reaction was concentrated to a yellow oil. The oil was purified by silca gel chromatography (10%-20% ethyl acetate in hexanes) to give the desired product (9.0 g).

Workup

  1. concentrationthe reaction was concentrated to a yellow oil
  2. customThe oil was purified by silca gel chromatography (10%-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7aa22a98ac8c4f91b4888ba208047683
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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