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

HRID 1289439Notes

Reaction equation

HRID 1289439 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]1[CH2:16][C:17](OC)=[O:18].O.[OH-].[Na+]>O1CCCC1>[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][CH:8]1[CH2:16][CH2:17][OH:18]

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 8028TetrahydrofuranSolvent2×

Procedure

Suspended in 100 ml of tetrahydrofuran were 1.02 g (26.8 mmol) of lithium aluminum hydride, and a solution of 5.06 g (26.6 mmol) of methyl (indan-2-yl)acetate in 10 ml of tetrahydrofuran was added dropwise to the suspension while chilling with ice water. After the addition, the mixture was stirred for 1 hour, and 1 ml of water, 1 ml of 15% sodium hydroxide and 3 ml of water were successively added dropwise to the mixture to decompose excess of the reducing agent. Solids were separated by filtration, the filtrate was concentrated, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4), thereby obtaining 4.30 g of a colorless oily substance. Yield: 100%.

Workup

  1. additionAfter the addition
  2. customSolids were separated by filtration
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)
  5. customobtaining 4.30 g of a colorless oily substance

Sources & evidence

ORD record
ord-915dc59cc4114cc29cb2349948bb1c29
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

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