Water → (1-methyl-1H-indol-2-yl)methanol

HRID 1601805

Reaction equation

HRID 1601805 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11](OC)=[O:12].[BH4-].[Li+].O>O1CCCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 258548methyl 1-methyl-1H-indole-2-carboxylateHCID 4148881Lithium borohydride

Product 1

HCID 295652(1-methyl-1H-indol-2-yl)methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.05 g of methyl 1-methylindole-2-carboxylate (prepared as described in Preparation 22) in 20 ml of anhydrous tetrahydrofuran was added dropwise to a mixture of 1.85 g of lithium borohydride and 80 ml of anhydrous tetrahydrofuran, and the resulting mixture was heated under reflux for 4 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 4.30 g of the title compound, melting at 92.8-95.2° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-e901d4ab86a7475ab7faa40ab4d78d76
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Linked notes

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