Hydrochloric Acid → HCID 86650675, compound

HRID 1643526Notes

Reaction equation

HRID 1643526 reaction equation
[C:1]([Mg]Br)#[CH:2].[CH3:5][C:6]1[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[C:7]=1[CH2:13][CH:14]=[O:15].Cl>C1COCC1>[CH3:5][C:6]1[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[C:7]=1[CH2:13][CH:14]([OH:15])[C:1]#[CH:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86650674HCID 86650674, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 86650675HCID 86650675, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethynylmagnesium bromide in THF (0.5 M, 210.0 ml, 105.0 mmol) was placed in a reactor under a nitrogen atmosphere at room temperature and (3-Methyl-bicyclo[2.2.1]hept-2-en-2-yl)-acetaldehyde (12.15 g, 80.9 mmol) in THF (200 ml) was introduced over a 90 minutes period and the mixture turned orange. The mixture was further stirred at room temperature for 30 minutes and was hydrolyzed with aqueous HCl 5% at room temperature. The mixture was extracted twice with Et2O and the combined organic layers were washed twice with a saturated aqueous solution of NaHCO3, H2O, and brine and dried over Na2SO4. Solvents were removed under vacuum to give a crude which was purified by flash chromatography with cyclohexane/AcOEt (95/5) as eluent to afford the title compound (11.32 g) in 79% yield.

Workup

  1. extractionThe mixture was extracted twice with Et2O
  2. washthe combined organic layers were washed twice with a saturated aqueous solution of NaHCO3, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. customSolvents were removed under vacuum
  5. customto give a crude which
  6. customwas purified by flash chromatography with cyclohexane/AcOEt (95/5) as eluent

Sources & evidence

ORD record
ord-8cf92636b78342349334648a8edd1bd8
Source dataset
uspto-grants-2012_02
Patent number
US08119826B2

Reaction notes

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