Calcium Carbonate → HCID 9952742, compound

HRID 1743402Notes

Reaction equation

HRID 1743402 reaction equation
[OH:1][C:2]1[C:3]([CH2:17][C:18]([CH3:20])=[CH2:19])=[C:4]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[N:7]([CH:13]=[O:14])[C:6]([CH3:16])([CH3:15])[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][CH2:19][C:18]1([CH3:20])[O:1][C:2]2[C:3](=[C:4]3[C:8](=[C:9]([CH3:12])[C:10]=2[CH3:11])[N:7]([CH:13]=[O:14])[C:6]([CH3:15])([CH3:16])[CH2:5]3)[CH2:17]1

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 22238076HCID 22238076, compoundHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 9952742HCID 9952742, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dihydro-5-hydroxy-2,2,6,7-tetramethyl-4-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (1.60 g, 5.85 mmol) in dichloromethane (15 mL) and methanol (5 mL) were added calcium carbonate (0.76 g, 7.6 mmol) and benzyltrimethylammonium dichloroiodate (2.24 g, 6.44 mmol), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was filtered and concentrated under reduced pressure. To the residue was added a 5% aqueous sodium hydrogen sulfite solution (15 mL), and the mixture was extracted with ethyl acetate two times. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to basic silica gel column chromatography (hexane-ethyl acetate 10:1) to obtain 1.93 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 sodium hydrogen sulfite solution (15 mL)
  4. extractionthe mixture was extracted with ethyl acetate two times
  5. washThe combined organic layers were washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c908b9d3818455985aad7a11abf5971
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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