Water → 1-Indanmethanol

HRID 1424707Notes

Reaction equation

HRID 1424707 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.C(OCC)(=O)C>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

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-HCID 21226445Aluminium lithium hydride

Product 1

HCID 2718801-IndanmethanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 mg (0.92 mmol) of indan-1-carboxylic acid compound was dissolved in 9 mL of tetrahydrofuran, and then 105 mg (2.77 mmol) of lithium aluminum hydride was added at 0° C. and stirred at room temperature for 2 hours. Water was slowly added to quench the reaction, and when a gel was formed by adding ethyl acetate, the celite was filtered. Then, the residue was dissolved again in 20 mL of ethyl acetate and the organic layer was washed with distilled water three times. The organic layer was dried with anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 124 mg of colorless oil (yield: 91%).

Workup

  1. customto quench
  2. customthe reaction, and when a gel
  3. customwas formed
  4. filtrationthe celite was filtered
  5. dissolutionThen, the residue was dissolved again in 20 mL of ethyl acetate
  6. washthe organic layer was washed with distilled water three times
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c2cfa26d2d64c7181a9012a10ab40aa
Source dataset
uspto-grants-2015_01
Patent number
US08927760B2

Reaction notes

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