Triphenylphosphine → Triphenylphosphine Oxide

HRID 538324Notes

Reaction equation

HRID 538324 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([Br:15])[N:9]=1)([OH:7])[CH3:6])=[N+]=[N-].[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.C(OCC)C>[Br:15][C:10]1[N:9]=[C:8]([C:5]2([CH3:6])[CH2:4][NH:1]2)[C:13]([F:14])=[CH:12][CH:11]=1.[CH:32]1[CH:33]=[CH:34][C:29]([P:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:7])=[CH:30][CH:31]=1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 86668033HCID 86668033, compound

Product 2

HCID 13097Triphenylphosphine OxideHCID 86668034HCID 86668034, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-azido-2-(6-bromo-3-fluoro-pyridin-2-yl)-propan-2-ol (11.2 g, 40.7 mmol) in THF (60 ml) was added triphenylphosphine (10.68 g, 40.7 mmol) and the reaction mixture was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue obtained was dissolved in diethylether and filtered through a cotton plug to remove triphenylphosphine oxide. The filtrate was washed with citric acid (9.6 g in 20 ml of water) and the organic phase was separated. The aqueous layer was made basic with 2N NaOH and extracted with diethylether. The organic layer was dried over sodium sulfate, filtered and evaporated to yield the title compound with some TPPO present: 8.1 g yellow oil (69% yield). TLC (cyclohexane/ethyl acetate 2:1) Rf=0.28; LCMS RtH6=0.46 (ES+ 231, 233); 1H-NMR (400 MHz, CDCl3): 7.34 (dd, 1H), 7.24 (dd, 1H), 1.99 (s, 1H), 1.89 (s, 1H), 1.65 (s, 3H, CH3).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue obtained
  3. filtrationfiltered through a cotton plug
  4. customto remove triphenylphosphine oxide
  5. washThe filtrate was washed with citric acid (9.6 g in 20 ml of water)
  6. customthe organic phase was separated
  7. extractionextracted with diethylether
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-ab72204fffa345ad8d5d6b89b7febb5e
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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