Acetone → HCID 86584563, compound

HRID 1794791Notes

Reaction equation

HRID 1794791 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH3:23][C:24]([CH3:26])=[O:25]>>[CH2:15]([O:14][C:12]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][CH2:23][CH:24]3[CH2:26][O:25]3)[CH:3]=2)[NH:7][C:6]=1[CH3:11])=[O:13])[CH3:16]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 820731H-Indole-3-carboxylic acid, 5-hydroxy-2-methyl-, ethyl ester

Product 1

HCID 86584563HCID 86584563, compound

Procedure

A solution of 2.19 g (10 mmol) of ethyl 5-hydroxy-2-methyl-indole-3-carboxylate, 2.6 g (10 mmol) of 2S(+)glycidyl-3-nitrobenzenesulfonate and 1.5 g (11 mmol) of potassium carbonate in 25 mL reagent grade acetone was refluxed overnight. The mixture was then allowed to cool to room temperature and the solids were removed by vacuum filtration. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organics were washed once with water, twice with brine, dried over sodium sulfate and concentrated in vacuo. Then the solid was dried under vacuum to give 2.65 g of the title compound as a dull tan solid; mp 93–94° C.; 1H NMR (300 MHz, CDCl3) δ 1.44 (t, J=5.3 Hz, 3H), 2.71 (s, 3H), 2.74–2.80 (m, 1H), 2.92 (t, J=4.7 Hz, 1H), 3.37–3.43 (m, 1H), 4.00–4.06 (m, 1 H), 4.27–4.31 (m, 1H), 4.37 (q, J=5.3 Hz, 2H), 6.86 (dd, J=5.5, 3.0 Hz, 1H), 7.18 (d, J=8.7 Hz, 1H), 7.67 (d, J=3.0 Hz, 1H), 8.32 (s, 1H); MS (ES) m/z: 275.9 (MH+); HRMS Calcd. for C15H18NO4(MH+): 276.1236. Found: 276.1228.

Workup

  1. customthe solids were removed by vacuum filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organics were washed once with water, twice with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThen the solid was dried under vacuum

Sources & evidence

ORD record
ord-571182c227924ef6acce33c6d6bbf8d0
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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