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

HRID 749295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749295
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 47776784-Benzyloxy-1-methyl-1H-indole-2-carboxylic acidAusbeute 102,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-da3afa501c324a0eb7e5f56e6ccb7866
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402604B2

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