Triphenylphosphine → HCID 86727990, compound

HRID 330768Notes

Reaction equation

HRID 330768 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[F:9][C:10]([F:15])([F:14])[CH2:11][CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][C:10]([F:15])([F:14])[F:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 1375123,3,3-Trifluoro-1-propanolHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 86727990HCID 86727990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1.00 g (5.75 mmol) 2-bromo-5-hydroxypyridine, 0.66 g (5.75 mmol) 3,3,3-trifluoro-1-propanol and 1.51 g (5.75 mmol) triphenylphosphine are added to 50 mL THF. Then 1.32 g (5.75 mmol) di-tert-butyl azodicarboxylate are added and the reaction mixture is stirred at 60° C. for 3 h. The solvent is removed in vacuo and the crude product is purified by column chromatography (silica gel, PE/EtOAc).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude product is purified by column chromatography (silica gel, PE/EtOAc)

Sources & evidence

ORD record
ord-cd5bab2c4d1043679748f40bca7bbd6f
Source dataset
uspto-grants-2014_11
Patent number
US08877741B2

Reaction notes

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