Water → HCID 15448801, compound

HRID 1871936Notes

Reaction equation

HRID 1871936 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([C:9]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:13]2)=[O:8].C1(C)C=CC(S(O[CH2:34][C@@H:35]2[O:37][CH2:36]2)(=O)=O)=CC=1.O>CN(C)C=O>[O:37]1[CH2:36][C@@H:35]1[CH2:34][O:18][C:17]1[C:9]([CH:7]=[O:8])=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 11064318HCID 11064318, compound

Product 1

HCID 15448801HCID 15448801, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (0.89 g) was added under nitrogen to a stirred solution of ethyl 4-formyl-5-hydroxyindole-2-carboxylate (1.50 g) in dry dimethylformamide (40 ml). A solution of (R)-glycidyl 4-toluenesulphonate (1.47 g) in dry dimethylformamide (30 ml) was then added and the mixture stirred at ambient temperature for 10 minutes, then at 60° C. for 3 hours. The mixture was poured into water (400 ml) and extracted with ethyl acetate (3×200 ml). The combined extracts were washed with brine (6×200 ml), dried over magnesium sulphate and the solvent evaporated under reduced pressure. The brown solid residue was purified by flash column chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate to give ethyl (R)-5-(2,3-epoxypropoxy)-4-formylindole-2-carboxylate (1.07 g) as an off-white solid; m.p. 152-154° C.

Workup

  1. waitat 60° C. for 3 hours
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe combined extracts were washed with brine (6×200 ml)
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent evaporated under reduced pressure
  6. customThe brown solid residue was purified by flash column chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate

Sources & evidence

ORD record
ord-b3f7e5d6a1184962a788b8aa349d1a9f
Source dataset
uspto-grants-2000_08
Patent number
US06107310

Reaction notes

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