Water → (Indolin-3-yl)methanol

HRID 74567Notes

Reaction equation

HRID 74567 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([C:10](OCC)=[O:11])[CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][OH:11])[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 19697859HCID 19697859, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22392033(Indolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.79 g (3.5 mmol) ethyl 2,3-dihydro-1H-indol-3-carboxylate were added batchwise at RT to 7.8 mL (7.8 mmol) of a 1 M lithium aluminium hydride solution (in THF) in 40 mL THF and refluxed for 1 h. Then the reaction mixture was combined with water while being cooled, the precipitate formed was filtered off and the filtrate was evaporated down.

Workup

  1. temperaturerefluxed for 1 h
  2. temperaturewhile being cooled
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. customthe filtrate was evaporated down

Sources & evidence

ORD record
ord-e16ed823924a41b9a87d54b3aff9207e
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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