Hydrochloric Acid → HCID 22506829, compound

HRID 985598Notes

Reaction equation

HRID 985598 reaction equation
[I:1][CH2:2][C:3]1([CH3:19])[O:18][C:6]2=[C:7]([CH3:17])[C:8]3[CH2:9][CH2:10][N:11](C=O)[C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1.Cl.C(=O)([O-])O.[Na+]>CO.O>[I:1][CH2:2][C:3]1([CH3:19])[O:18][C:6]2=[C:7]([CH3:17])[C:8]3[CH2:9][CH2:10][NH:11][C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22506845HCID 22506845, compound

Product 1

HCID 22506829HCID 22506829, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3,5,6,7-Tetrahydro-2-(iodomethyl)-2,4,8-trimethyl-2H-furo[2,3-f]indole-5-carbaldehyde (3.71 g, 10 mmol) was dissolved in methanol (37 ml). To the solution was added concentrated hydrochloric acid, and stirred for 2 hours at 60° C. under argon atmosphere. The mixture was cooled to 0° C., made weakly basic with a saturated aqueous solution of sodium hydrogen carbonate, diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate, and the solvent was removed under reduced pressure, and this was subjected to chromatography on a small amount of silica gel with eluting with ethyl acetate. The resultant oil was crystallized from hexane to obtain 3.37 g of the title compound.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. washwith eluting with ethyl acetate
  7. customThe resultant oil was crystallized from hexane

Sources & evidence

ORD record
ord-625b6a9bc83041e88102bc9f364920e3
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

Loading…