Water → 2-(2,3-dihydro-1H-inden-2-yl)ethanol

HRID 1654941Notes

Reaction equation

HRID 1654941 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1.O.[OH-].[Na+]>O1CCCC1>[CH2:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH:11]1[CH2:10][CH2:9][OH:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14090225Methyl (2,3-dihydro-1H-inden-2-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 103520002-(2,3-dihydro-1H-inden-2-yl)ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.02 g (26.8 mmol) of lithium aluminum hydride was suspended in 100 ml of tetrahydrofuran, to which was added dropwise a solution of 10 ml tetrafuran containing 5.06 g (26.6 mmol) of methyl(indan-2-yl)acetate under ice-cooling. After completion of the addition, stirring was continued for 1 hour, during which 1 ml water, 1 ml of 15% sodium hydroxide and 3 ml water were added dropwise in this order for decomposing the excessive reducing agent. The solid matter was removed by filtration, the filtrate was condensed and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 4.30 g of a colorless oil. Yield: 100%

Workup

  1. temperaturecooling
  2. additionAfter completion of the addition
  3. additionwere added dropwise in this order
  4. customThe solid matter was removed by filtration
  5. customcondensed
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-f03b3b53196c4a62a31e3c2dc29dff39
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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