Hydrochloric Acid → HCID 21194440, compound

HRID 564988Notes

Reaction equation

HRID 564988 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[C:7]([CH2:12][O:13]C3CCCCO3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]>O1CCCC1>[OH:13][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[C:4]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:3]2[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21194188HCID 21194188, compound

Product 1

HCID 21194440HCID 21194440, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In a solvent mixture of 20 ml of 2N hydrochloric acid and 60 ml of tetrahydrofuran was dissolved 4.00 g (12.6 mmol) of ethyl 1-methyl-4-(2-tetrahydropyranyl)oxymethyl-2-indolecarboxylate. The solution was stirred at 50° C. for an hour. The reaction mixture was poured onto ice water and the aqueous layer was extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium hydrogen-carbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 2.90 g (99%) of ethyl 4-hydroxymethyl-1-methyl-2-indolecarboxylate.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined extracts were washed with saturated sodium hydrogen-carbonate solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-455ac6ee32e74d44a61e35f8c5475057
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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