Triphenylphosphine → 3-(3,5-Difluorophenoxy)tetrahydro-2H-pyran

HRID 1499611Notes

Reaction equation

HRID 1499611 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[O:10]1[CH2:15][CH2:14][CH2:13][CH:12](O)[CH2:11]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>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[O:9][CH:12]1[CH2:13][CH2:14][CH2:15][O:10][CH2:11]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 759283,5-DifluorophenolHCID 5363146Diisopropyl azodicarboxylateHCID 12256033tetrahydro-2H-pyran-3-ol

Product 1

HCID 867268303-(3,5-Difluorophenoxy)tetrahydro-2H-pyranYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,5-difluorophenol (1.15 g, 8.81 mmol), tetrahydro-2H-pyran-3-ol (0.900 g, 8.81 mmol), triphenylphosphine (2.31 g, 8.81 mmol) and DIAD (1.74 mL, 8.81 mmol) in THF (10 mL) was stirred overnight. The solution was then concentrated under reduced pressure and the residue was purified by purified by column chromatography on silica gel using CombiFlash® apparatus eluting with EtOAc/hexanes (0-30%). The purification afforded 1.43 g (75.8%) of the sub-title compound as a colorless oil.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. customthe residue was purified
  3. customby purified by column chromatography on silica gel using CombiFlash® apparatus
  4. washeluting with EtOAc/hexanes (0-30%)
  5. customThe purification

Sources & evidence

ORD record
ord-b73e56504dc64af9833bbf63bd5b1540
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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