Sodium Sulfate → 1-(2-Fluorophenyl)propan-2-ol

HRID 2084745Notes

Reaction equation

HRID 2084745 reaction equation
C(N(C(C)C)C(=O)[O:6][CH:7]([CH3:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])(C)C.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH:7]([OH:6])[CH3:16]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 12070578HCID 12070578, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 120705791-(2-Fluorophenyl)propan-2-olYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, to a solution of 5.11 g (18.2 mmol) of 2-(2-fluorophenyl)-1-methylethyl diisopropylcarbamate in THF, a 1.0M solution of 182 ml (182 mmol) of diisobutylaluminum hydride in THF was added dropwise. The reaction mixture was stirred overnight at room temperature and sodium sulfate 10-hydrate was slowly added until no effervescence was observed. After addition of the sodium sulfate, the mixture was filtered, the filtrate was distilled off and purified by silica gel column chromatography, giving 2.15 g of the title compound. (Yield: 77% yield, 97% ee)

Workup

  1. filtrationthe mixture was filtered
  2. distillationthe filtrate was distilled off
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-60749c987bbd45f1a4f92e1ef5ac1616
Source dataset
uspto-grants-2004_04
Patent number
US06717016B2

Reaction notes

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