Magnesium perchlorate → Methyl 3-(5-methoxy-1H-indol-3-yl)propanoate

HRID 2100451Notes

Reaction equation

HRID 2100451 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12]O.[CH3:14][O:15][C:16]([O:20][Si](C)(C)C)=[C:17](C)C.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>ClCCl.O>[CH3:14][O:15][C:16](=[O:20])[CH2:17][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1

Participants

6

Reactant 3

HCID 24840Magnesium perchlorateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 4255293(5-methoxy-1H-indol-3-yl)methanol

Product 1

HCID 54357260Methyl 3-(5-methoxy-1H-indol-3-yl)propanoateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-methoxy-1H-indol-3-yl-methanol 141 (115 mg, 0.643 mmol) dissolved in dichloromethane (3 ml), (1-methoxy-2-methyl-propenyloxy)-trimethylsilane (200 mg, 1 mmol) and magnesium perchlorate (164 mg, 0.74 mmol) were added. The reaction was allowed to stir at ambient temperature for 3-4 hours after after which the mixture was diluted with water (50 ml) and dichloromethane (DCM, 100 mL). The organic layer was separated and washed with water (50 mL; 3×). The organic layer was washed once with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give an oil and purified with flash chromatography (silica with 80% hexane, 20% ethyl acetate to afford 142 as a light colored oil (150 mg; 88% yield; M+1=262.3).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (50 mL; 3×)
  3. washThe organic layer was washed once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. custompurified with flash chromatography (silica with 80% hexane, 20% ethyl acetate

Sources & evidence

ORD record
ord-e91f4878fcbd4e9c9f8123fe4501f66e
Source dataset
uspto-grants-2009_08
Patent number
US07572806B2

Reaction notes

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