2-Phenylethanol → 3-Acetyl-5-chloro-1-phenethylindole

HRID 2270970Notes

Reaction equation

HRID 2270970 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:33](O)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[N:6]([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 60542-PhenylethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27629711-(5-chloro-1H-indol-3-yl)ethanone

Product 1

HCID 129686353-Acetyl-5-chloro-1-phenethylindoleYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.58 g (3 mmol) of 3-acetyl-5-chloroindole, 1.42 g (5.4 mmol) of triphenylphosphine and 0.66 g (5.4 mmol) of phenethyl alcohol in THF (12 ml) was added under ice-cooling, 1.09 g (5.4 mmol) of diisopropyl azodicarboxylate. After stirring for 3 hours at room temperature, the mixture was concentrated under reduced pressure. The obtained residue was chromatographed on silica gel (1/4 ethyl acetate/toluene as eluant) to give 0.58 g of the titled compound as an oil. Yield: 65%.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe obtained residue was chromatographed on silica gel (1/4 ethyl acetate/toluene as eluant)

Sources & evidence

ORD record
ord-c0e267bbb3c347e38d37dac1d733be82
Source dataset
uspto-grants-2001_12
Patent number
US06333323B1

Reaction notes

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