Ethyl Acetate → Benzenepropanoic acid, 4-bromo-β-hydroxy-, ethyl ester

HRID 1006880Notes

Reaction equation

HRID 1006880 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].[Li].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.[Cl-].[NH4+]>O1CCCC1.C1CCCCC1>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[CH2:2][C:1]([O:4][CH2:5][CH3:6])=[O:3])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 707414-BromobenzaldehydeHCID 3028194Lithium

Product 1

HCID 12566304Benzenepropanoic acid, 4-bromo-β-hydroxy-, ethyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

Ethyl acetate (5.8 ml) was dissolved in tetrahydrofuran (80 ml), to which was then added 1.5M lithium diisoprypylamide/cyclohexane solution (43 ml) in nitrogen atmosphere at −70° C., and then the mixture was stirred for 15 min. 4-Bromobenzaldehyde (10.151 g)/tetrahydrofuran (10 ml) solution was added to the reaction mixture, which was then stirred for 30 min. A saturated aqueous solution of ammonium chloride was added thereto, and then it was extracted with in ethyl acetate. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (11.906 g, yield; 80%).

Workup

  1. customat −70° C.
  2. stirringwas then stirred for 30 min
  3. extractionit was extracted with in ethyl acetate
  4. washThe resulting organic layer was washed with water
  5. dry with materialdried (over MgSO4)
  6. customevaporated
  7. customThe resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-3bea6f4857554779b32e3544dfa1a32c
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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