Potassium Carbonate → (1-Methyl-1H-indol-7-yloxy)-acetic acid ethyl ester

HRID 1009017Notes

Reaction equation

HRID 1009017 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][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:2]([CH3:1])[CH:3]=[CH:4]2)[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 221368021-methyl-1H-indol-7-ol

Product 1

HCID 67304817(1-Methyl-1H-indol-7-yloxy)-acetic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-1-H-indol-7-ol (Chemstep, CAS: 47577-334, 2.5 g, 17 mmol) and ethyl iodoacetate (Fluka, CAS: 623-48-3, 4.58 g, 21 mmol) in DMF abs. (25 mL) was added potassium carbonate (4.23 g, 31 mmol). The reaction mixture was stirred at rt for 20 h, quenched with ice/water, and extracted with ethyl acetate. The organics were washed, dried and concentrated, the residue was chromatographed on silica gel using heptanelethyl acetate as eluent to obtain the desired compound (3.37 g) as a creamy solid. MS (ISP): m/e 234.1 (M+H)+

Workup

  1. customquenched with ice/water
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was chromatographed on silica gel using heptanelethyl acetate as eluent

Sources & evidence

ORD record
ord-a31fab5e8e3c47a8838aa07a1e1c47f2
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

Loading…