Water → 5-(prop-2-en-1-yloxy)-1H-indole

HRID 1527167Notes

Reaction equation

HRID 1527167 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17](Br)[CH:18]=[CH2:19].O>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)[CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 160545-Hydroxyindole

Product 1

HCID 142392305-(prop-2-en-1-yloxy)-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-hydroxyindole (1.23 g, 9.24 mmol) and cesium carbonate (3.01 g, 9.24 mmol) in DMF (40 mL) under nitrogen atmosphere at 0° C. was added allylbromide (879 μl, 10.16 mmol). The reaction mixture was stirred at RT for 2 h and poured into water and extracted with EtOAc (×3). The combined organic layers were washed twice with water, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 9:1) to give the desired compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.76; tR (conditions a): 3.46 min.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washThe combined organic layers were washed twice with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-96a20e0f4bfe44eabdeb96593fb27693
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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