Triphenylphosphine → HCID 69034312, compound

HRID 2251868Notes

Reaction equation

HRID 2251868 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.O[C@H:16]1[CH2:20][CH2:19][O:18][CH2:17]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:8]([C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:5]=1)[O:1][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 69034312HCID 69034312, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

3-Hydroxy-5-nitrobenzotrifluoride (5 g, 24.1 mmol, 1 eq), (S)-3-hydroxytetrahydrofuran (1.9 mL, 24.1 mmol, 1 eq), PPh3 (6.3 g, 24.1 mmol, 1 eq) were dissolved in 43 mL of THF. The solution was cooled to −20° C. DIAD (4.8 mL, 24.6 mmol, 1.02 eq) was added in 22 mL of THF over the course of 2 h while the temperature was maintained between −10 and −20° C. After the addition was complete the reaction was stirred for 3 days at RT. The solvent was removed in vacuo. The residue was stirred with ˜250 mL of hexane for 45 min during which time triphenylphosphine oxide precipitated as a white solid. The solid was removed by filtration and the filtrate was washed twice with 2 N NaOH and once with brine. After drying over Na2SO4 the solution was filtered and the solvent removed under reduced pressure. The crude material was purified by chromatography on a Biotage system eluting with a gradient of 5 to 15% EtOAc:hexane to yield the desired compound.

Workup

  1. temperaturewas maintained between −10 and −20° C
  2. additionAfter the addition
  3. customThe solvent was removed in vacuo
  4. stirringThe residue was stirred with ˜250 mL of hexane for 45 min during which time triphenylphosphine oxide
  5. customprecipitated as a white solid
  6. customThe solid was removed by filtration
  7. washthe filtrate was washed twice with 2 N NaOH and once with brine
  8. dry with materialAfter drying over Na2SO4 the solution
  9. filtrationwas filtered
  10. customthe solvent removed under reduced pressure
  11. customThe crude material was purified by chromatography on a Biotage system
  12. washeluting with a gradient of 5 to 15% EtOAc

Sources & evidence

ORD record
ord-170df6c23c4c46b292b4e56e20a19046
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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