Calcium Carbonate → HCID 22506845, compound

HRID 985597Notes

Reaction equation

HRID 985597 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:8](=[C:9]([CH3:15])[C:10]=1[CH2:11][C:12]([CH3:14])=[CH2:13])[N:7]([CH:16]=[O:17])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[Ca+2].[I:24](Cl)(=O)=O.I(Cl)(=O)=O.C[NH+](C)C>CO.C1COCC1>[I:24][CH2:13][C:12]1([CH3:14])[O:1][C:2]2=[C:3]([CH3:18])[C:4]3[CH2:5][CH2:6][N:7]([CH:16]=[O:17])[C:8]=3[C:9]([CH3:15])=[C:10]2[CH2:11]1

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 22506833HCID 22506833, compoundHCID 86759630HCID 86759630, compound

Product 1

HCID 22506845HCID 22506845, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2,3-Dihydro-5-hydroxy-4,7-dimethyl-6-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (4.17 g, 17.0 mmol) was dissolved in methanol-THF solution (34 ml, 1:1). To the mixture was added calcium carbonate (2.21 g, 22.1 mmol) and then trimethylammonium dichloroiodate (6.51 g, 18.7 mmol) was added. After stirring for 1 hour at room temperature, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was combined a 10% aqueous solution of sodium thiosulfate, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain 5.52 g of the title compound.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b47d854687f54ac29a94022ef5cd55ee
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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