Ethanol → HCID 19799307, compound

HRID 2081176Notes

Reaction equation

HRID 2081176 reaction equation
[Na].C(O)C.[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[CH2:6][CH3:7].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1>C(O)C.O1CCCC1>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][C:5](=[O:8])[CH:6]([CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)[CH3:7])[CH3:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 703202-BromomethylnaphthaleneHCID 78656Ethyl 3-oxovalerateHCID 5360545Sodium

Product 1

HCID 19799307HCID 19799307, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Sodium (1.25 g) was added to 60 mL of absolute ethanol under nitrogen atmosphere at room temperature. When all of the metal had reacted the mixture was cooled in ice and ethyl propionylacetate was added in one portion. The reaction mixture was brought to reflux temperature for 0.25 hours, an ethanol-tetrahydrofuran solution (10:1, 120 mL) of 2-bromomethylnaphthalene (10 g) added, and the resulting mixture heated at reflux temperature 15 hours. The reaction mixture was cooled to room temperature and the volatile materials removed in vacuo on the rotary evaporator. The residue was partitioned between saturated, aqueous NaCl solution and ethyl acetate. The organic phase was dried over MgSO4 and concentrated to an oily mixture which was purified by HPLC (hexane, ethyl acetate gradient elution) to give 5.2 g of ethyl-α-(2-naphthalenylmethyl)propionylacetate as a yellow oil.

Workup

  1. customWhen all of the metal had reacted the mixture
  2. temperaturewas cooled in ice
  3. temperatureto reflux temperature for 0.25 hours
  4. temperaturethe resulting mixture heated
  5. temperatureat reflux temperature 15 hours
  6. customthe volatile materials removed in vacuo on the rotary evaporator
  7. customThe residue was partitioned between saturated, aqueous NaCl solution and ethyl acetate
  8. dry with materialThe organic phase was dried over MgSO4
  9. concentrationconcentrated to an oily mixture which
  10. customwas purified by HPLC (hexane, ethyl acetate gradient elution)

Sources & evidence

ORD record
ord-d6162b57fc7c4fe9b85e48937f974433
Source dataset
uspto-grants-1993_02
Patent number
US05183825

Reaction notes

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