Calcium Carbonate → HCID 22506878, compound

HRID 985600Notes

Reaction equation

HRID 985600 reaction equation
[OH:1][C:2]1[C:3]([CH3:20])=[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])[C:6]([CH3:19])([CH3:18])[CH2:5]2.C(=O)([O-])[O-].[Ca+2].[I:26](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>ClCCl.CO>[I:26][CH2:13][C:12]1([CH3:14])[O:1][C:2]2=[C:3]([CH3:20])[C:4]3[CH2:5][C:6]([CH3:19])([CH3:18])[N:7]([CH:16]=[O:17])[C:8]=3[C:9]([CH3:15])=[C:10]2[CH2:11]1

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 22506835HCID 22506835, compoundHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 22506878HCID 22506878, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dihydro-5-hydroxy-2,2,4,7-tetramethyl-6-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (1.90 g, 6.95 mmol) in dichloromethane (20 ml) and methanol (10 ml) were added calcium carbonate (0.90 g, 9.0 mmol) and benzyltrimethylammonium dichloroiodate (2.66 g, 7.64 mmol), and stirred for 15 minutes at room temperature. The reaction mixture was filtered and concentrated under reduced pressure. To the residue was added a 5% aqueous solution of sodium hydrogen sulfite (15 ml), and extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine and water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain 2.40 g of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added a 5% aqueous solution of sodium hydrogen sulfite (15 ml)
  4. extractionextracted twice with ethyl acetate
  5. washwashed with saturated brine and water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b357f43d1fad498994784d733f43700e
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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