Triphenylphosphine → HCID 58071887, compound

HRID 870516Notes

Reaction equation

HRID 870516 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[C:6]#[N:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:31]1[CH2:36][CH2:35][CH:34](O)[CH2:33][CH2:32]1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>O1CCCC1.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:34]1[CH2:35][CH2:36][O:31][CH2:32][CH2:33]1)[C:6]#[N:7]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 781354-Hydroxy-3-methoxybenzonitrileHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate

Product 1

HCID 58071887HCID 58071887, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8 g 3-Methoxy-4-hydroxy-benzonitrile, 28.1 g triphenylphosphine and 5.48 g tetrahydro-4H-pyran-4-ol was suspended in 1 L tetrahydrofuran at 0° C. before 24.7 g di-tert-butylazodicarboxylate (DBAD) was added over 30 min. The reaction was warmed to ambient temperature and stirred for 2 d. After this time, the reaction was diluted with water and ethyl acetate. The organic phase was separated and then it was washed with 1N sodium hydroxide, water and saturated sodium chloride, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel chromatography (SiO2: heptane/ethyl acetate 8:2 to 7:3) to provide the title compound.

Workup

  1. additionwas added over 30 min
  2. customThe organic phase was separated
  3. washit was washed with 1N sodium hydroxide, water and saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified on silica gel chromatography (SiO2: heptane/ethyl acetate 8:2 to 7:3)

Sources & evidence

ORD record
ord-5e7495d6f38e433e8292e4acdcd6b92e
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

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