Water → HCID 22036415, compound

HRID 493305Notes

Reaction equation

HRID 493305 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[CH2:11]1[O:13][CH2:12]1.[H-].[Na+].O>O1CCOCC1>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[O:1][CH2:11][CH2:12][OH:13])[CH:7]=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 6354Ethylene OxideHCID 24758Sodium hydrideHCID 27376517-Hydroxyindole

Product 1

HCID 22036415HCID 22036415, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-hydroxyindole (1.00 g, 7.51 mmol) and ethylene oxide (0.33 g, 7.50 mmol) in dioxane (3 mL) was placed in a reaction tube. NaH (60% in oil; 0.100 g, 2.45 mmol) was added and the reaction mixture was stirred at 100° C. for 5 days. The reaction mixture was poured into water, extracted with EtOAc, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel using toluene/EtOAc (1:1) as eluent to give 0.45 g (34%) of the title product. Pos-EI-MS shows M+ and 5 ions supporting the stated structure. HRMS m/z calcd for C10H11NO2 (M)+ 177.0790, found 177.0799.

Workup

  1. customwas placed in a reaction tube
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a54f99468ab54a05a30c52591bdd6b2a
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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