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

HRID 1764887Notes

Reaction equation

HRID 1764887 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11](OCC)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC.CCOC(C)=O.[O-]S([O-])(=O)=O.[Mg+2]>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[CH2:10][CH2:11][OH:12]

Participants

7

Reactant 3

HCID 962WaterHCID 10104359Ethyl 2-(2,3-dihydro-1H-inden-2-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 103520002-(2,3-dihydro-1H-inden-2-yl)ethanol

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 24083Sulfuric acid magnesium salt (1:1)Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2,3-dihydro-1H-inden-2-ylacetate (285 mg, 1.39 mmol) in Et2O (5 mL) at 0° C. under N2 was added LAH (53 mg, 1.39 mmol). After stirring for 40 minutes at 0° C., 0.4 mL of H2O was added to quench the reaction. The reaction mixture was diluted with EtOAc (100 mL) and MgSO4 was added with stirring. The reaction mixture was then filtered and concentrated in vacuo to a clear oil. 2-(2,3-dihydro-1H-inden-2-yl)ethanol was isolated without further purification.

Workup

  1. customto quench
  2. customthe reaction
  3. additionwas added
  4. stirringwith stirring
  5. filtrationThe reaction mixture was then filtered
  6. concentrationconcentrated in vacuo to a clear oil

Sources & evidence

ORD record
ord-b3a625809a514b65994dfe9873c578c1
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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