Calcium Carbonate → HCID 9820740, compound

HRID 1743401Notes

Reaction equation

HRID 1743401 reaction equation
[OH:1][C:2]1[C:3]([CH2:15][C:16]([CH3:18])=[CH2:17])=[C:4]2[C:8](=[C:9]([CH3:12])[C:10]=1[CH3:11])[N:7]([CH:13]=[O:14])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[Ca+2].[I:24](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>ClCCl.CO>[I:24][CH2:17][C:16]1([CH3:18])[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])[CH2:6][CH2:5]3)[CH2:15]1

Participants

6

Reactant 3

HCID 10112Calcium CarbonateHCID 22238067HCID 22238067, compoundHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 9820740HCID 9820740, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2,3-dihydro-5-hydroxy-6,7-dimethyl-4-(2-methyl-2-propenyl)-1H-indole-1-carbaldehyde (4.91 g, 20.0 mmol) in dichloromethane (10 mL) and methanol (20 mL) was added calcium carbonate (2.60 g, 26.0 mmol), the mixture was ice-cooled, a solution of benzyltrimethylammonium dichloroiodate (7.66 g, 22.0 mmol) in dichloromethane (20 mL) was added dropwise over 10 minutes under nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered, and concentrated under reduced pressure. To the residue was added a solution of sodium hydrogen sulfite (2.50 g) in water (50 mL), and the mixture was extracted with ethyl acetate three 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 silica gel column chromatography (hexane-ethyl acetate 5;1 then 2:1), and recrystallized from ethyl acetate-diisopropyl ether to obtain 4.34 g of the title compound.

Workup

  1. temperaturecooled
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added a solution of sodium hydrogen sulfite (2.50 g) in water (50 mL)
  5. extractionthe mixture was extracted with ethyl acetate three times
  6. washThe combined organic layers were washed with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. custom2:1), and recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-ac669700a0b74a73962f9051fb7fa298
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

Loading…