Water → 2-Phenyl-1-propanol

HRID 1417806

Reaction equation

HRID 1417806 reaction equation
C1(C[C@H]2COC(=O)N2[C:14](=[O:23])[CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:17]1([CH:15]([CH3:16])[CH2:14][OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 56980759(4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone

Product 1

HCID 142952-Phenyl-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of (4S)-4-(phenylmethyl)-3-(2-phenylpropionyl)-2-oxazolidinone (XLI, Isomer I, 2.651 g, 8.57 mmol) in THF (10 ml) is added dropwise to a cooled slurry of lithium aluminum hydride (0.3518 g, 9.27 mmol) in THF (10 ml). After the mixture had stirred for 28 min at 0°, water (0.35 ml) is added and the mixture is stirred for 15 min. Sodium hydroxide (15% aqueous solution, 0.35 ml) is added and again the mixture is allowed to stir for 15 min. After the final addition of water (1.05 ml), the salts are removed by filtration and washed with ether. The combined filtrates are washed with saline, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel eluting with ethyl acetate/hexane (15/85). The appropriate fractions are pooled and concentrated to give 2-phenylpropanol (XLIII, Isomer Ia), NMR (CDCl3) 1.28, 1.35, 2.95, 3.71 and 7.26 δ.

Workup

  1. stirringthe mixture is stirred for 15 min
  2. stirringto stir for 15 min
  3. customthe salts are removed by filtration
  4. washwashed with ether
  5. washThe combined filtrates are washed with saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel eluting with ethyl acetate/hexane (15/85)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-54957f7148bf443bb1dc3b27d1e40d92
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Linked notes

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