Hydrochloric Acid → HCID 9929328, compound

HRID 1743403Notes

Reaction equation

HRID 1743403 reaction equation
[I:1][CH2:2][C:3]1([CH3:21])[O:14][C:13]2[C:5](=[C:6]3[C:10](=[C:11]([CH3:16])[C:12]=2[CH3:15])[N:9](C=O)[C:8]([CH3:20])([CH3:19])[CH2:7]3)[CH2:4]1.Cl.C(=O)(O)[O-].[Na+]>CO.O.C(OCC)(=O)C>[I:1][CH2:2][C:3]1([CH3:21])[O:14][C:13]2[C:5](=[C:6]3[C:10](=[C:11]([CH3:16])[C:12]=2[CH3:15])[NH:9][C:8]([CH3:20])([CH3:19])[CH2:7]3)[CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 9952742HCID 9952742, compound

Product 1

HCID 9929328HCID 9929328, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a solution of 1,6,7,8-tetrahydro-2-(iodomethyl)-2,4,5,7,7-pentamethyl-2H-furo[3,2-e]indole-6-carbaldehyde (1.93 g, 4.83 mmol) in methanol (10 mL) was added concentrated hydrochloric acid (3 mL), and the mixture was heated to reflux for 3 hours under the nitrogen atmosphere. The reaction mixture was added dropwise to a mixture of sodium bicarbonate (3.7 g, 44 mmol) in water-ethyl acetate to neutralize, which 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 silica gel column chromatography (hexane-ethyl acetate 10:1) to obtain 1.56 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours under the nitrogen atmosphere
  3. extractionwhich was extracted with ethyl acetate two times
  4. washThe combined organic layers were washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c5b71c1df18414f801d02923a160ed1
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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