HCID 18677103, compound → 2,3-Dihydro-1H-indene-2-carbaldehyde

HRID 1634110Notes

Reaction equation

HRID 1634110 reaction equation
CON(C)[C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 18677103HCID 18677103, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 117447712,3-Dihydro-1H-indene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred ice-cold solution of the above amide (400 mg, 1.9 mmol) in ether (20 mL), was added lithium aluminium hydride (1 M in THF, 4 mL). After stirring the ice-cold mixture for 1 h, excess reducing agent was quenched by the careful addition of 1N sulfuric acid (10 mL). The reaction mixture was stirred for 5min, the ether layer was decanted and the remaining solid was washed with ether (100 mL). The combined ether extract was washed with water, dried over anhydrous sodium.sulfate, and evaporated to give indane 2-carboxaldehyde as a light brownish oil which was used without further purification in the next step.

Workup

  1. customwas quenched by the careful addition of 1N sulfuric acid (10 mL)
  2. customthe ether layer was decanted
  3. washthe remaining solid was washed with ether (100 mL)
  4. extractionThe combined ether extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium
  7. customsulfate, and evaporated

Sources & evidence

ORD record
ord-0621dc93e5de446c8e8e608e845c2f1e
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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