Water → 1-Indanmethanol

HRID 1253797

Reaction equation

HRID 1253797 reaction equation
[CH:1]1([C:10](O)=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]1([CH2:10][OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-HCID 21226445Aluminium lithium hydride

Product 1

HCID 2718801-IndanmethanolYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dihydro-1H-inden-1-carboxylic acid (0.50 g) in tetrahydrofuran (5.0 mL), lithium aluminum hydride (0.18 g) was added under ice-cooling and the resultant reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture, water was added under ice-cooling and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate=85:15 to 75:25) to obtain the subject compound (445 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. customthe resultant reaction mixture
  3. temperaturecooling
  4. customthe resultant reaction mixture
  5. extractionwas extracted with ethyl acetate
  6. washThe organic phase was washed with a saturated saline
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  9. customthe resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate=85:15 to 75:25)

Sources & evidence

ORD record
ord-7035823aa91149e1850c5c847de48d58
Source dataset
uspto-grants-2013_06
Patent number
US08455500B2

Linked notes

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