Triphenylphosphine Oxide → 2-(1-{4-[1-(4-Iodophenyl)-1,2-dimethylpropyl]phenoxy}-1-methylethyl)pyridine

HRID 1025808Notes

Reaction equation

HRID 1025808 reaction equation
S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:48]2[CH:64]=[CH:63][C:51]([O:52][C:53]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=3)([CH3:56])[CH2:54]O)=[CH:50][CH:49]=2)([CH3:47])[CH:44]([CH3:46])[CH3:45])=[CH:39][CH:38]=1.[BH4-].[Na+]>C(Cl)Cl>[I:36][C:37]1[CH:38]=[CH:39][C:40]([C:43]([C:48]2[CH:49]=[CH:50][C:51]([O:52][C:53]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=3)([CH3:54])[CH3:56])=[CH:63][CH:64]=2)([CH3:47])[CH:44]([CH3:45])[CH3:46])=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 4311764Sodium borohydrideHCID 583812432-{4-[1-(4-Iodophenyl)-1,2-dimethylpropyl]phenoxy}-2-pyridin-2-ylpropan-1-ol

Product 1

HCID 583812252-(1-{4-[1-(4-Iodophenyl)-1,2-dimethylpropyl]phenoxy}-1-methylethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of triflic anhydride (1 equiv.) in DCM is added to a solution of triphenylphosphine oxide (2 equiv) in DCM at 0° C. After precipitation is observed (˜15 min), a solution of 5e (1 equiv) in DCM is added. After 5 min, sodium borohydride (4 equiv.) is added in one portion. After completion of reaction, the reaction mixture is quenched with 2 N HCl, poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5f.

Workup

  1. customAfter precipitation
  2. custom(˜15 min)
  3. customAfter completion of reaction
  4. customthe reaction mixture is quenched with 2 N HCl
  5. additionpoured into saturated aqueous sodium bicarbonate
  6. extractionextracted three times with EtOAc
  7. washThe combined organic extracts are washed with water, brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customPurification of the crude residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-daa997b9f5544517b134d48485c6103d
Source dataset
uspto-grants-2014_05
Patent number
US08729104B2

Reaction notes

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