Hydrochloric Acid → HCID 22506876, compound

HRID 985601Notes

Reaction equation

HRID 985601 reaction equation
[I:1][CH2:2][C:3]1([CH3:21])[O:20][C:6]2=[C:7]([CH3:19])[C:8]3[CH2:9][C:10]([CH3:18])([CH3:17])[N:11](C=O)[C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1.Cl.C(=O)([O-])O.[Na+].O.C(OCC)(=O)C>CO>[I:1][CH2:2][C:3]1([CH3:21])[O:20][C:6]2=[C:7]([CH3:19])[C:8]3[CH2:9][C:10]([CH3:17])([CH3:18])[NH:11][C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22506878HCID 22506878, compoundHCID 22728543Water ethylacetate

Product 1

HCID 22506876HCID 22506876, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,3,6,7-tetrahydro-2-(iodomethyl)-2,4,6,6,8-pentamethyl-5H-furo[2,3-f]indole-5-carbaldehyde (2.42 g, 6.06 mmol) in methanol (10 ml) was added concentrated hydrochloric acid (3 ml), and heated under reflux for 2.5 hours under nitrogen atmosphere. The reaction mixture was added dropwise to a mixture of sodium hydrogen carbonate (3.7 g, 44 mmol) with water-ethyl acetate, neutralized and extracted three times with ethyl acetate. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain 2.20 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours under nitrogen atmosphere
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aef4d9e3002e42e894949aeeef8b6547
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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