1-Bromo-3-chloropropane → 4-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester

HRID 2042625Notes

Reaction equation

HRID 2042625 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:8])[CH3:2].Br[CH2:18][CH2:19][CH2:20][Cl:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:18][CH2:19][CH2:20][Cl:21])=[CH:13][CH:14]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 114359904-(4-Hydroxyphenyl)-4-oxo-butyric acid ethyl ester

Product 1

HCID 596520284-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 1 L round bottom flask, 4-(4-hydroxyphenyl)-4-oxo-butyric acid ethyl ester (8.65 g, 39.0 mmol), 1-bromo-3-chloro-propane (6.1 g, 61.0 mmol), and potassium carbonate (9.3 g, 67.1 mmol) in acetonitrile (300 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, separated and dried over MgSO4. Purification with silica gel chromatography eluting with hexanes/ethyl acetate (3:1) produced 7.9 g (68%). MS m/z 299 (M+H).

Workup

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customPurification with silica gel chromatography
  8. washeluting with hexanes/ethyl acetate (3:1)
  9. customproduced 7.9 g (68%)

Sources & evidence

ORD record
ord-a39f329cf64342c7b998e957275e03bc
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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