Ethanol sodium ethoxide → (2S,3R)-3-benzyl-2-oxiranecarboxylic acid

HRID 1173772Notes

Reaction equation

HRID 1173772 reaction equation
Cl[CH:2]([C@H:8]([OH:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].[O-]CC.[Na+].C(O)C>C(O)C>[CH2:9]([C@H:8]1[O:16][C@@H:2]1[C:3]([OH:5])=[O:4])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 23706232Ethanol sodium ethoxideHCID 59203390ethyl (3R)-2-chloro-3-hydroxy-4-phenylbutyrate

Product 1

HCID 22867771(2S,3R)-3-benzyl-2-oxiranecarboxylic acidYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (3R)-2-chloro-3-hydroxy-4-phenylbutyrate (122 mg, 0.5 mmol) was dissolved in ethanol (3 ml), and 20 wt % sodium ethoxide/ethanol solution (254 mg) was gradually added. The mixture was stirred at room temperature for 3 hours, and the solvent was evaporated away under reduced pressure. Water (5 ml) was added, and the pH was adjusted to 13 with 30 wt % aqueous solution of sodium hydroxide. The mixture was washed with toluene (5 ml), and the pH was adjusted to 1.5 with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate (15 ml), and drying was carried out with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain the title compound as a brown oil (66 mg, yield: 74%).

Workup

  1. customthe solvent was evaporated away under reduced pressure
  2. additionWater (5 ml) was added
  3. washThe mixture was washed with toluene (5 ml)
  4. extractionThe mixture was extracted with ethyl acetate (15 ml)
  5. customdrying
  6. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-2be5878217154bf38257c8eb262b7001
Source dataset
uspto-grants-2010_11
Patent number
US07834190B2

Reaction notes

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