Citric Acid → tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 2422242Notes

Reaction equation

HRID 2422242 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](OC)=[O:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][OH:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 299461281-tert-Butyl 3-methyl 1H-indole-1,3-dicarboxylateHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 11075767tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylateYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(tert-butoxycarbonyl)-1H-indole-3-carboxylate (2.5 g, 9.08 mmol) in anhydrous tetrahydrofuran (40 ml) was added 1.5 M diisobutylaluminum hydride-toluene solution (14 ml, 21 mmol) under ice-cooling, and the mixture was stirred for 2 hrs. An aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was washed successively with aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (2.3 g, 100%) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fbaecb139f954bea84ac99428f5debb2
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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