Hydrochloric Acid → 2,3-dihydro-1H-indol-2-ylmethanol

HRID 7421

Reaction equation

HRID 7421 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10](O)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.Cl>O1CCCC1>[OH:11][CH2:10][CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86074Indoline-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27946642,3-dihydro-1H-indol-2-ylmethanolYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (RS)-indoline-2-carboxylic acid (8.16 g, 50 mmol) in tetrahydrofuran (50 ml) was added under ice-cooling lithium aluminum hydride (5.7 g, 150 mmol) and the mixture was stirred at 60° C. for 18 h. The reaction mixture was stirred under ice-cooling and ethanol and 1N hydrochloric acid were added. The precipitate was filtered off and the mother liquor was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was applied to silica gel column chromatography and eluted with ethyl acetate-hexane (1:4-1:1) to give the title compound (4.8 g, 64%).

Workup

  1. stirringThe reaction mixture was stirred under ice-
  2. temperaturecooling
  3. filtrationThe precipitate was filtered off
  4. washthe mother liquor was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washeluted with ethyl acetate-hexane (1:4-1:1)

Sources & evidence

ORD record
ord-44c45998a8b849329f98083d33b92282
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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