Triphenylphosphine → HCID 58072009, compound

HRID 870510Notes

Reaction equation

HRID 870510 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>O1CCCC1.O>[O:33]1[CH2:38][CH2:37][CH:36]([O:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:11])([F:12])[F:13])[CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 74956Tetrahydro-4H-pyran-4-ol2×HCID 27831594-hydroxy-3-(trifluoromethyl)benzonitrileHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate2×

Product 1

HCID 58072009HCID 58072009, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

2 g 4-Hydroxy-3-trifluoromethyl-benzonitrile, 5.6 g triphenylphosphine and 1.2 g tetrahydro-4H-pyran-4-ol was suspended in 15 mL tetrahydrofuran at 0° C. before 4.92 g di-tert-butylazodicarboxylate (DBAD) as a solution in 5 mL tetrahydrofuran was added over 15 min. The reaction was warmed to ambient temperature. Additional 2.8 g triphenylphosphine, 0.55 g (5.3 mmol) tetrahydro-4H-pyran-4-ol and 2.46 g di-tert-butylazodicarboxylate (DBAD) in tetrahydrofuran were added and the reaction was stirred overnight. After this time, the reaction was diluted with water and extracted with ethyl acetate (×2). The organic phase was separated and then it was washed with 2N sodium hydroxide, water and saturated sodium chloride, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel chromatography (SiO2: heptane/ethyl acetate) to provide the title compound.

Workup

  1. additionwas added over 15 min
  2. extractionextracted with ethyl acetate (×2)
  3. customThe organic phase was separated
  4. washit was washed with 2N sodium hydroxide, water and saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified with silica gel chromatography (SiO2: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-1b43951b297e4ff894af95918fc35668
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

Loading…