Methanol → 1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid

HRID 1833693Notes

Reaction equation

HRID 1833693 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][C:6]1([CH3:19])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)C.CO.[OH-].[K+]>O>[CH3:19][C:6]1([CH2:5][C:4]([OH:20])=[O:3])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 537142471-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester

Product 1

HCID 104905711-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrolysis of this ester to the title compound is effected as follows: The ester is dissolved in 230 ml. of methanol. To this is added 10 g. of KOH in 30 ml. of H2O and the solution is allowed to stand at room temperature overnight. The methanol is evaporated, water added and the solution washed with benzene. The aqueous phase is acidified with 6N HCl, and extracted with benzene. This organic phase is washed with water, dried over sodium sulfate and evaporated to dryness to give an oil, which is crystallized from benzene containing a trace of petroleum ether to afford the title compound, m.p. 150 - 152° C., νmaxCHCl3 3325 and 1705 cm-1.

Workup

  1. additionTo this is added 10 g
  2. customThe methanol is evaporated
  3. additionwater added
  4. washthe solution washed with benzene
  5. extractionextracted with benzene
  6. washThis organic phase is washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness
  9. customto give an oil, which
  10. customis crystallized from benzene containing a trace of petroleum ether

Sources & evidence

ORD record
ord-f0c6dbebf739464ea74213c7cf387657
Source dataset
uspto-grants-1978_01
Patent number
US04066780

Reaction notes

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