Acetic Anhydride → Acetic acid 2-(1-methyl-1H-indol-7-yloxy)-ethyl ester

HRID 1009015

Reaction equation

HRID 1009015 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][OH:14])[CH:4]=[CH:3]1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][O:14][C:15](=[O:17])[CH3:16])[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 673047412-(1-Methyl-1H-indol-7-yloxy)-ethanol

Product 1

HCID 67304991Acetic acid 2-(1-methyl-1H-indol-7-yloxy)-ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(1-methyl-1H-indol-7-yloxy)-ethanol (0.78 g, 4 mmol) in pyridine (10 mL) was treated with acetic anhydride (5 mL). The reaction mixture was stirred at rt for 4 h and concentrated. The residue was quenched with ice/water and extracted with ethyl acetate. The organics were washed with 2N sulfuric acid, sat. sodium bicarbonate and brine, dried and concentrated. The residue was chromatographed on silica gel using heptanelethyl acetate as eluent to produce the desired compound (0.90 g) as an off-white solid. MS (ISP): m/e 234.1 (M+H)+

Workup

  1. concentrationconcentrated
  2. customThe residue was quenched with ice/water
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with 2N sulfuric acid, sat. sodium bicarbonate and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel using heptanelethyl acetate as eluent

Sources & evidence

ORD record
ord-6df211154aa948ef91eb957b4b6645ce
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Linked notes

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