Lithium hydroxide, monohydrate → 4-Benzyloxy-1-methyl-1H-indole-2-carboxylic acid

HRID 749295Notes

Reaction equation

HRID 749295 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21]CC)=[O:20])[N:13]2[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([OH:21])=[O:20])[N:13]2[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22054863Ethyl 4-benzyloxy-1-methylindole-2-carboxylate

Product 1

HCID 47776784-Benzyloxy-1-methyl-1H-indole-2-carboxylic acidYield 102.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of ethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxylate (3.09 g) in THF (200 mL) was added LiOH.H2O (1.26 g) in water (200 mL) and the resulting two phase solution was heated at 45° C. under nitrogen overnight. The cooled reaction mixture was evaporated to remove THF and the remaining aqueous solution was acidified with NaHSO4 to precipitate the title compound, which was collected, washed with water, and dried to give 2.87 g of the title compound. Mp 216.6-216.8° C.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated
  3. customto remove THF
  4. customto precipitate the title compound, which
  5. customwas collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-da3afa501c324a0eb7e5f56e6ccb7866
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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