Triphenylphosphine → 5-Ethyl-2,4-dihydroxybenzaldehyde

HRID 1707307Notes

Reaction equation

HRID 1707307 reaction equation
C(C(C)(CCCCCO)C)#N.[OH:12][C:13]1[C:20](O)=[C:19](CC)[CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O:52][CH2:53][CH3:54])=O)=NC(OCC)=O>C1COCC1>[CH2:19]([C:18]1[C:53]([OH:52])=[CH:54][C:15]([OH:16])=[C:14]([CH:17]=1)[CH:13]=[O:12])[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18963024HCID 18963024, compoundHCID 18963047HCID 18963047, compound

Product 1

HCID 160888255-Ethyl-2,4-dihydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 50 mL dry THF solution of the above prepare 2-cyano-2-methyl-7-hydroxyheptane and 2,3-dihydroxy-4-ethylbenzaldehyde was stirred at room temp. To this solution added triphenylphosphine (17.91 g, 68.3 mmol) and finally diethyl azodicarboxylate (11.89 g, 68.3 mmol). The reaction was stirred at room temp for 2 h 15 min. and then quenched with saturated NH4Cl solution. The THF was removed under vacuum and the resulting residue was dissolved in EtOAc and the EtOAc solution was washed with brine. The organic layer was dried over MgSO4. Filtration and solvent removal gave an orange solid. The product was purified by Waters Prep 500 chromatography using silica gel as a solid support and eluting with a gradient of 10% to 30% EtOAc/Hexane over 50 min. The desired product was obtained as a yellow oil (10.50 g, 51%).

Workup

  1. stirringThe reaction was stirred at room temp for 2 h 15 min.
  2. customquenched with saturated NH4Cl solution
  3. customThe THF was removed under vacuum
  4. dissolutionthe resulting residue was dissolved in EtOAc
  5. washthe EtOAc solution was washed with brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationFiltration and solvent removal
  8. customgave an orange solid
  9. customThe product was purified by Waters Prep 500 chromatography
  10. washeluting with a gradient of 10% to 30% EtOAc/Hexane over 50 min

Sources & evidence

ORD record
ord-bfa9cfc1c9954af4bc8a859c92b91b17
Source dataset
uspto-grants-1994_10
Patent number
US05352690

Reaction notes

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