Ethanol → HCID 23157947, compound

HRID 1817206Notes

Reaction equation

HRID 1817206 reaction equation
S(=O)(=O)(O)O.[Br:6][CH:7]([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:8]([OH:10])=[O:9].O.[CH2:23](O)[CH3:24]>>[Br:6][CH:7]([CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:8]([O:10][CH2:23][CH3:24])=[O:9]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 23157961HCID 23157961, compound

Product 1

HCID 23157947HCID 23157947, compound

Procedure

Concentrated sulfuric acid (1 ml) was added to a solution of the 2-bromo-5-(4-methoxyphenyl)pentanoic acid crude product (Reference Example 37) (1000 mg) in ethanol (15 ml) at room temperature and the resulting mixture was heated under reflux for 2 hours. After being allowed to cool to room temperature, the reaction solution was poured into water (50 ml) and extracted with ethyl acetate (50 ml). The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution (30 ml) and a saturated aqueous sodium chloride solution (30 ml) and then dried over sodium sulfate. The dried organic layer was concentrated under reduced pressure and the crude product thus obtained was purified by HPLC to obtain ethyl 2-bromo-5-(4-methoxyphenyl)pentanoate (740 mg).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate (50 ml)
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution (30 ml)
  5. dry with materiala saturated aqueous sodium chloride solution (30 ml) and then dried over sodium sulfate
  6. concentrationThe dried organic layer was concentrated under reduced pressure
  7. customthe crude product thus obtained
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-7d6c3d3046154096939118d4ee241daa
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

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