Potassium Carbonate → 2-(1-Methyl-1H-indol-7-yloxy)-ethanol

HRID 1009014Notes

Reaction equation

HRID 1009014 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3]1.I[CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:13][CH2:14][OH:15])[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 221368021-methyl-1H-indol-7-ol

Product 1

HCID 673047412-(1-Methyl-1H-indol-7-yloxy)-ethanolYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-1-H-indol-7-ol (Chemstep, CAS: 47577-33-4, 0.98 g, 6.8 mmol) and 2-iodoethanol (Fluka, 1.60 g, 8.6 mmol)) in DMF abs. (10 mL) was added potassium carbonate (1.84 g, 13 mmol). The reaction mixture at rt for 20 h, then at 70° C. for 24 h, quenched with ice/water, extracted with ethyl acetate. The organics were washed, dried and concentrated, the residue chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain the desired compound (0.82 g) as a creamy solid. MS (ISP): m/e 192.3 (M+H)+

Workup

  1. waitat 70° C. for 24 h
  2. customquenched with ice/water
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-068634ef49c644ab833e080f7776d332
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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