Water → 4-(2-Fluorophenyl)-3-hydroxy-2-methylbutane-1,3-diol

HRID 2084738Notes

Reaction equation

HRID 2084738 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][CH:15]([OH:23])[CH:16]([CH3:22])[C:17]([O:19]CC)=O.[OH2:24].[OH-].[Na+]>O1CCCC1.CCOCC>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([OH:23])([OH:24])[CH:16]([CH3:22])[CH2:17][OH:19]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 12070572HCID 12070572, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 227346504-(2-Fluorophenyl)-3-hydroxy-2-methylbutane-1,3-diolYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Under a nitrogen atmosphere, 2.84 g (74.9 mmol) of lithium aluminum hydride was added to 30 ml of tetrahydrofuran (hereinafter, referred to as THF). A solution of 18.0 g of ethyl 4-(2-fluorophenyl)-3-hydroxy-2-methylbutanoate in 180 ml of THF was added thereto. After stirring for 1.5 hr at room temperature, 5 ml of water and 5 ml of 1N-NaOH aqueous solution were added thereto successively to quench the reaction. 100 ml of Et2O was added to the quenched reaction mixture, after stirring a while, the obtained suspension was filtered. The filtrate was distilled off and the residue was purified by silica gel column chromatography to obtain 14.5 g of the title compound as a colorless oil. (Yield: 99%)

Workup

  1. customsuccessively to quench
  2. customthe reaction
  3. stirringafter stirring a while
  4. filtrationthe obtained suspension was filtered
  5. distillationThe filtrate was distilled off
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-39a7aa65145845b78921affb6bf27784
Source dataset
uspto-grants-2004_04
Patent number
US06717016B2

Reaction notes

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