Lithium hydroxide, monohydrate → HCID 13491214, compound

HRID 1593637Notes

Reaction equation

HRID 1593637 reaction equation
C([O:3][C:4]([CH:6]1[CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>C1COCC1>[CH2:8]1[C:9]2[NH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH2:18][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 282360ethyl 2,3,4,9-tetrahydro-1h-carbazole-3-carboxylate

Product 1

HCID 13491214HCID 13491214, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid ethyl ester (34.5 g, 142 mol) was dissolved in 375 mL of THF. Lithium hydroxide hydrate (23.8 g, 566 mmol) was added. The mixture was stirred at room temperature 48 h, at which time TLC showed complete consumption of starting ester. The mixture was acidified with 1 N HCl and was extracted with ethyl acetate. The organic layer was washed with brine, then was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 30.4 g (99%) of the title compound.

Workup

  1. customconsumption of starting ester
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c19a7032bb34de38faba60d1dde4647
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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