Ethyl 2-bromopropionate → HCID 19419240, compound

HRID 864517Notes

Reaction equation

HRID 864517 reaction equation
[CH2:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11])[CH2:2][CH3:3].Br[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>O1CCCC1>[CH2:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 79040Ethyl 2-bromopropionateHCID 2620601,3-Benzenediol, propyl-

Product 1

HCID 19419240HCID 19419240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.08 g of a 60% oil dispersion, 27 mmoles) under an argon atmosphere was washed with 15 ml of dry hexane. The hexane supernatant was removed via syringe. Dry tetrahydrofuran (60 ml) was added to the sodium hydride and, with stirring at room temperature, the 2-propyl-1,3-dihydroxybenzene (4.08 g, 27 mmoles) was added as a 40 ml tetrahydrofuran solution. After stirring at room temperature for 25 minutes, the ethyl 2-bromopropionate (4.64 g, 26 mmoles) was added rapidly. After stirring at room temperature for 17 hours, the reaction was quenched with a saturated aqueous ammonium chloride solution and the tetrahydrofuran was removed under vacuum. The resulting aqueous mixture was extracted several times with ethyl acetate. The organic extract was dried over magnesium sulfate. Filtration and solvent removal gave an orange oil. This oil was purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexane. The desired title ester was obtained as a white solid (2.43 g, 36%).

Workup

  1. washSodium hydride (1.08 g of a 60% oil dispersion, 27 mmoles) under an argon atmosphere was washed with 15 ml of dry hexane
  2. customThe hexane supernatant was removed via syringe
  3. additionDry tetrahydrofuran (60 ml) was added to the sodium hydride
  4. stirringAfter stirring at room temperature for 25 minutes
  5. stirringAfter stirring at room temperature for 17 hours
  6. customthe reaction was quenched with a saturated aqueous ammonium chloride solution
  7. customthe tetrahydrofuran was removed under vacuum
  8. extractionThe resulting aqueous mixture was extracted several times with ethyl acetate
  9. extractionThe organic extract
  10. dry with materialwas dried over magnesium sulfate
  11. filtrationFiltration and solvent removal
  12. customgave an orange oil
  13. customThis oil was purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4610a4428cb24e6a9afe34255d031969
Source dataset
uspto-grants-1996_10
Patent number
US05563164

Reaction notes

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