5-Methoxyindole-3-carbaldehyde → (5-methoxy-1H-indol-3-yl)methanol

HRID 2100450Notes

Reaction equation

HRID 2100450 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]2[NH:11][CH:12]=[C:13]([CH:14]=[O:15])[C:7]=2[CH:6]=1>CO.C1COCC1.O.C(=O)([O-])[O-].[K+].[K+]>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[NH:11][CH:12]=[C:13]2[CH2:14][OH:15]

Participants

7

Reactant 2

HCID 827585-Methoxyindole-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 4255293(5-methoxy-1H-indol-3-yl)methanolYield 70%

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of sodium borohydride (2 grams, 0.05 mol) in methanol (15 ml), a solution of 5-methoxy-1H-indol-3-carboxaldehyde 2 (1 gram, 0.006 mol) dissolved in THF (20 ml) and methanol (15 ml) were combined and stirred at ambient temperature for 16 hours. The reaction was diluted with water and potassium carbonate (to saturation) and stirred to quench unreacted sodium borohydride. Diethyl ether was used to extract the product from the quenched solution. Following layers separation, the aqueous layer was further extracted (2×) with diethyl ether. The combined organic pats were dried over sodium sulfate and evaporated to dryness to yield a light colored solid 141 (736 mg, 70%).

Workup

  1. stirringstirred
  2. customto quench unreacted sodium borohydride
  3. extractionto extract the product from the quenched solution
  4. customFollowing layers separation
  5. extractionthe aqueous layer was further extracted (2×) with diethyl ether
  6. dry with materialThe combined organic pats were dried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-86a02e858a75486380ac4d511406cc85
Source dataset
uspto-grants-2009_08
Patent number
US07572806B2

Reaction notes

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