Ethyl Acetate → 3-(2-Fluorophenyl)propan-1-ol

HRID 2257833Notes

Reaction equation

HRID 2257833 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][C:16](OC)=[O:17].C(OCC)(=O)C.[Cl-].[NH4+]>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][CH2:16][OH:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 15479441Methyl 3-(2-fluorophenyl)propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 126185173-(2-Fluorophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.2 gm of lithium aluminum hydride was suspended in 110 ml of dried THF and stirred for 1 hour at room temperature. To the suspension was slowly added over 15 minutes a solution of 5 gm of the compound prepared in (2) above in 50 ml of THF. The mixture was stirred for 12 hours at room temperature, and after the addition of 20 ml of ethyl acetate, for a further 3 hours. Then, 5 ml of saturated aqueous solution of ammonium chloride was added to the mixture, followed by further stirring for 30 minutes. After removing the precipitate by filtration, the filtrate was washed with water and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 4.27 gm of the title compound.

Workup

  1. stirringThe mixture was stirred for 12 hours at room temperature
  2. waitfor a further 3 hours
  3. stirringby further stirring for 30 minutes
  4. customAfter removing the precipitate
  5. filtrationby filtration
  6. washthe filtrate was washed with water
  7. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-32f5d42ac7c34ff5aa3a2f4cc1af2a64
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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