1,5-Dibromopentane → HCID 54246863, compound

HRID 328038Notes

Reaction equation

HRID 328038 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=2)[CH:10]=[CH:9][C:8]=1[OH:24])[CH3:2].[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:24][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][Br:26])[CH3:2]

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 54185689HCID 54185689, compound

Product 1

HCID 54246863HCID 54246863, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1.08 g (3.12 mmol) of 7-(2-ethoxy-2-oxoethoxy)-2-hydroxy-1-naphthalenepropanoic acid ethyl ester from the preceding example, 4.31 g (18.7 mmol) of 1,5-dibromopentane, 2.59 g (18.7 mmol) of anhydrous granular potassium carbonate, and 70 mL of 2-butanone was heated at 65° C. for 24 hr. After being cooled to room temperature, the mixture was filtered through anhydrous magnesium sulfate. The solids were washed thoroughly with ethyl acetate and the filtrate and the washes were combined and concentrated in vacuo. To the residue was added 60 mL of ethanol and 1 mL of concentrated sulfuric acid and the resulting solution was stirred at room temperature for 17.5 hr. Most of the ethanol was removed under reduced pressure and the residue was flash chromatographed on 110 g of silica gel, eluting with hexane-ethyl acetate (6:1) to give 1.15 g (74.4%) of the title compound as an off-white, waxy solid, mp 29.5°-32° C.

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationthe mixture was filtered through anhydrous magnesium sulfate
  3. washThe solids were washed thoroughly with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. additionTo the residue was added 60 mL of ethanol and 1 mL of concentrated sulfuric acid
  6. customMost of the ethanol was removed under reduced pressure
  7. customchromatographed on 110 g of silica gel
  8. washeluting with hexane-ethyl acetate (6:1)

Sources & evidence

ORD record
ord-e118ab43727642358ba4e76b013ae7c6
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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