Tryptophol → HCID 18186837, compound

HRID 1357600Notes

Reaction equation

HRID 1357600 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:5]=2[CH:6]=1.[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=1>O1CCOCC1.ClCCl>[Cl:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([O:12][CH2:11][CH2:10][C:7]2[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[NH:9][CH:8]=2)[N:15]=1

Participants

5

Reactant 2

HCID 10685TryptopholHCID 785042,6-Dichloropyrazine

Product 1

HCID 18186837HCID 18186837, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

K-t-BuO (2.32 g, 20.6 mmol) was added to a stirred solution of tryptophol (1.7 g, 10.6 mmol) in dioxane (30 mL) at 0° C. (ice-bath). After being stirred for 10 min at 0° C. and 10 min at room temperature, the mixture was chilled to 0° C. (ice-bath) and 2,6-dichloropyrazine (1.37 g, 9.17 mmol) was added. The yellowish reaction mixture was stirred at 0° C. for 30 min and for a further 20 min at room temperature. The mixture was diluted with dichloromethane, filtered, and concentrated in vacuo to furnish a brownish oil. This material was purified by chromatography on silica gel (14×5 cm) using n-hexane/ethyl acetate (75:25). This furnished 1.38 g (55%) of the title compound as a beige solid. Purity>90% by 1H NMR in CDCl3.

Workup

  1. additionwas added
  2. customThe yellowish reaction mixture
  3. stirringwas stirred at 0° C. for 30 min and for a further 20 min at room temperature
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto furnish a brownish oil
  7. customThis material was purified by chromatography on silica gel (14×5 cm)

Sources & evidence

ORD record
ord-9fd446b0fa814a6282a24fbb401de170
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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