Triphenylphosphine → HCID 57791770, compound

HRID 1091703Notes

Reaction equation

HRID 1091703 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1.[CH:8]1(O)[CH2:11][CH2:10][CH2:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH:8]1([O:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 76218CyclobutanolHCID 5363146Diisopropyl azodicarboxylateHCID 178418642HCID 178418642, compound

Product 1

HCID 57791770HCID 57791770, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridin-4-ol (6.0 g, 63.09 mmol), cyclobutanol (5.00 g, 69.40 mmol) and triphenylphosphine (18.20 g, 69.40 mmol) were added to THF (250 mL) and stirred for 10 minutes. To this was slowly added diisopropylazodicarboxylate (13.49 mL, 69.40 mmol). Once the addition was complete the reaction was stirred at 50° C. for 1 hour. The solvent was evaporated and the crude residue was dissolved in diethyl ether. To this was added a small amount of triphenylphoshine oxide and the reaction was stirred for 30 minutes to afford a solid, this was filtered and discarded. The solvent was evaporated and the pale yellow gum was acidified with 2.0M HCl, extracted with diethyl ether (1×75 mL) and the aqueous was then basified with solid potassium hydroxide. This was then extracted with diethyl ether (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford yellow gum. This was purified by distillation at 0.60 mBar, collecting fractions that distilled at 80° C. to afford the desired compound as a colourless oil (4.70 g, 49.9%); 1H NMR (400.132 MHz, CDCl3) δ 1.78-1.66 (1H, m), 1.95-1.86 (1H, m), 2.24-2.14 (2H, m), 2.51-2.43 (2H, m), 4.69 (1H, quintet), 6.70 (2H, d), 8.40 (2H, d); m/z (LC-MS, ESI+), RT=1.76 (M+H 150).

Workup

  1. additionOnce the addition
  2. stirringwas stirred at 50° C. for 1 hour
  3. customThe solvent was evaporated
  4. dissolutionthe crude residue was dissolved in diethyl ether
  5. additionTo this was added a small amount of triphenylphoshine oxide
  6. stirringthe reaction was stirred for 30 minutes
  7. customto afford a solid
  8. filtrationthis was filtered
  9. customThe solvent was evaporated
  10. extractionextracted with diethyl ether (1×75 mL)
  11. extractionThis was then extracted with diethyl ether (3×75 mL)
  12. dry with materialthe organic layer was dried over MgSO4
  13. filtrationfiltered
  14. customevaporated
  15. customto afford yellow gum
  16. distillationThis was purified by distillation at 0.60 mBar
  17. customcollecting fractions
  18. distillationthat distilled at 80° C.

Sources & evidence

ORD record
ord-03c1fd61a8f045f2bee0f2da251a510c
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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