Sodium sulfate decahydrate → (+)-1-(2-Fluorophenyl)-3-methylbutane-2-ol

HRID 2084740Notes

Reaction equation

HRID 2084740 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(C1C=CC(C)=CC=1)(O[CH2:11][CH:12]([CH3:23])[CH:13]([OH:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])(=O)=O.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH:13]([OH:22])[CH:12]([CH3:11])[CH3:23]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 120705744-(2-Fluorophenyl)-3-hydroxy-2-methylbutyl tosylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12070575(+)-1-(2-Fluorophenyl)-3-methylbutane-2-olYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 2.28 g (60.2 mmol) of lithium aluminum hydride was added to 30 ml of THF. A solution of 21.1 g (60.2 mmol) of 4-(2-fluorophenyl)-3-hydroxy-2-methylbutyl tosylate in 210 ml of THF was added dropwise thereto at room temperature. After stirring for 0.5 hr at room temperature, sodium sulfate 10 hydrate was added slowly until no effervescence was observed. 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 9.6 g of the title compound as a colorless solid. (Yield: 88%) An optical purity was determined to be 98.1% ee by GC using Chirasil DEX CB according to a conventional method.

Workup

  1. customat room temperature
  2. stirringAfter stirring a while
  3. filtrationthe obtained suspension was filtered
  4. distillationthe filtrate was distilled off
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dff483d126904b2e9036cc0a115e0c81
Source dataset
uspto-grants-2004_04
Patent number
US06717016B2

Reaction notes

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