Methyl 1H-indole-2-carboxylate → (1H-indol-2-yl)methanol

HRID 2365870Notes

Reaction equation

HRID 2365870 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[C:20](OC)=[O:21]>C1COCC1>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[CH2:20][OH:21]

Participants

4

Reactant 2

HCID 70992Methyl 1H-indole-2-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 98783(1H-indol-2-yl)methanolYield 102.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminum hydride (159 mL, 159 mmol) was added dropwise at −60° C. to a solution of methyl 1H-indole-2-carboxylate (10.0 g, 52.9 mmol) in THF (100 mL). After being stirred for 1 hour, the reaction was quenched with saturated NH4Cl. The resulting mixture was extracted with ethyl acetate (2×100 mL) and washed with brine, dried, and concentrated to give (1H-indol-2-yl)methanol (8.0 g, 100% yield) as a solid. LCMS (ESI) m/z: 148.1 [M+H]+.

Workup

  1. customthe reaction was quenched with saturated NH4Cl
  2. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a512385056c94b1dbef55cbcd54af861
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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