Ethanol → 1-(2,2-Diethoxyethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylic Acid

HRID 1021891Notes

Reaction equation

HRID 1021891 reaction equation
[CH2:1]([O:3][CH:4]([O:20][CH2:21][CH3:22])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]1[C:15]([O:17]CC)=[O:16])[CH3:2].C(O)C.O1CCCC1.[OH-].[Na+]>O>[CH2:21]([O:20][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]1[C:15]([OH:17])=[O:16])[CH3:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86683752Ethyl 1-(2,2-Diethoxyethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Product 1

HCID 866837531-(2,2-Diethoxyethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylic AcidYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 195b (4.7 g, 15.2 mmol) in a mixed solvent of ethanol (20 mL), tetrahydrofuran (20 mL), and water (30 mL) was added sodium hydroxide (3.0 g, 75.0 mmol). The reaction was heated at 75° C. for two days and concentrated under reduced pressure. The residue was suspended in water and neutralized with diluted aqueous citric acid solution. The mixture was extracted with ethyl acetate (3×100 mL) and the combined organic phase was concentrated under reduced pressure to afford 195c (3.32 g, 78%). MS-ESI: [M-EtOH+H]+ 236.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  3. concentrationthe combined organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3a510303efbf45d680428440aa9d7b74
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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