Ethanol → 130251-07-9

HRID 2194296Notes

Reaction equation

HRID 2194296 reaction equation
S(=O)(=O)(O)O.[Br:6][C@H:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9].[CH2:13](O)[CH3:14]>>[Br:6][C@H:7]([CH2:11][CH3:12])[C:8]([O:10][CH2:13][CH3:14])=[O:9]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 6992738alpha-Bromobutyric acid, (R)-

Product 1

HCID 7000062130251-07-9

Procedure

0.45 mL of sulfuric acid was added to ethanol (70 mL) solution of 7.0 g of (R)-2-bromobutyric acid at room temperature, and refluxed for 3 hours. The reaction mixture was cooled to room temperature, and poured into ice water (140 mL). The solution was extracted 3 times with ethyl acetate. The combined extract was sequentially washed with saturated sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, and 7.47 g of the subject compound was prepared as colorless oil. Optical purity 96% ee (HPLC)

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionThe solution was extracted 3 times with ethyl acetate
  3. extractionThe combined extract
  4. washwas sequentially washed with saturated sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo, and 7.47 g of the subject compound
  8. customwas prepared as colorless oil

Sources & evidence

ORD record
ord-254f7db1dc424391b1abd5787be0b820
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

Loading…