Ethyl Acetate → 1H-indol-4-ylmethanol

HRID 1352006Notes

Reaction equation

HRID 1352006 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[NH:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20](OC)=[O:21])[C:14]=2[CH:13]=[CH:12]1.C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[NH:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:20][OH:21])[C:14]=2[CH:13]=[CH:12]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2733668methyl 1H-indole-4-carboxylateHCID 9855836Potassium sodium tartarateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 27734571H-indol-4-ylmethanolYield 101.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

Diisobutylaluminum hydride (1 M in toluene; 1.3 mL, 1.3 mmol) was added to a solution of 1H-indole-4-carboxylic acid, methyl ester (85 mg, 0.49 mmol) in ether (1.6 mL) at −70° C. The solution was allowed to stir at −70° C. for 1 h, then at room temperature for 1 h. Ethyl acetate (20 mL) was added, and the solution was stirred with an aqueous solution of potassium sodium tartrate (30% w/v; 20 mL) for 30 min. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, evaporated, and dried under high vacuum to give 1H-indole-4-methanol (73.2 mg, quantitative yield) which was used in the next step without further purification.

Workup

  1. waitat room temperature for 1 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-09447eaf0a364804b870a040162588f2
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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