Toluene → HCID 15878269, compound

HRID 377439Notes

Reaction equation

HRID 377439 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].C([C:14](=[O:18])[C:15]([O-:17])=[O:16])CCC.C(=O)(O)[O-].[Na+].[C:24]1(C)[CH:29]=CC=[CH:26][CH:25]=1>>[OH:18][CH:14]([CH2:3][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:1])[C:15]([O:17][CH2:29][CH2:24][CH2:25][CH3:26])=[O:16]

Participants

5

Reactant 4

HCID 1140TolueneHCID 7407Alpha-MethylstyreneHCID 516892Sodium BicarbonateHCID 6419709HCID 6419709, compound

Product 1

HCID 15878269HCID 15878269, compoundYield 82%

Procedure

To 118 mg (1 mmol) of α-methylstyrene and 130 mg (1 mmol) of n-butylglyoxylate was added at 0° C. the solution of the complex in toluene obtained in Example 1 (2). After stirring for 1 hour, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and filtered through celite. Then the filtrate was extracted with ether thrice and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1). Thus 213 mg of n-butyl 2-hydroxy-4-phenyl-4-pentenoate was obtained (yield: 82%). When measured with CHIRALPAK AS column (manufactured by Daicel Chemical Industries) [hexane:i-PrOH=3:1, flow rate: 0.5 ml/min], the optical purity of this product was 97.5% e.e.

Workup

  1. filtrationfiltered through celite
  2. extractionThen the filtrate was extracted with ether thrice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-bbd8e9d95f0e413fbf6d54d9b0c683b0
Source dataset
uspto-grants-2000_02
Patent number
US06025503

Reaction notes

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