Hydrochloric Acid → HCID 12538348, compound

HRID 849058Notes

Reaction equation

HRID 849058 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]1[O:13][CH:10]1[CH:11]=[CH2:12].Cl>CCOCC.C1COCC1>[C:1]1([CH2:12][CH:11]=[CH:10][CH2:9][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13586VinyloxiraneHCID 178418255HCID 178418255, compound

Product 1

HCID 12538348HCID 12538348, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a -10° C. solution of phenylmagnesium bromide, 3M in ether (68 mL) was added a solution of cupric acetate (5.6 g) and butadiene monoxide (6.43 mL) in THF (200 mL) over 40 min while maintaining the reaction temperature below -5° C. The reaction was stirred at -10° C. for 1 h, room temperature for 16 h, refluxed for 15 min then cooled to room temperature. Aqueous HCl (10%, 100 mL) was added and the mixture extracted with ethyl acetate. The organic solution was washed with aqueous HCl (10%), NaHCO3 (saturated) and brine (saturated), dried (MgSO4) and concentrated to yield a blue liquid. The residue was chromatographed to yield the title compound (6.3 g, 30%).

Workup

  1. temperaturewhile maintaining the reaction temperature below -5° C
  2. temperaturerefluxed for 15 min
  3. temperaturethen cooled to room temperature
  4. extractionthe mixture extracted with ethyl acetate
  5. washThe organic solution was washed with aqueous HCl (10%), NaHCO3 (saturated) and brine (saturated)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto yield a blue liquid
  9. customThe residue was chromatographed

Sources & evidence

ORD record
ord-5a9f0badd84c4a13bf646c064c811c4a
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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