Triphenylphosphine → 4-Chloro-2-[[(1r)-4-chloro-1-phenylbutyl]oxy]benzonitrile

HRID 352103Notes

Reaction equation

HRID 352103 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32]C1C=CC(C#N)=C(O)C=1.C(O)(=O)C(O)=O.[Cl:48][C:49]1[CH:56]=[CH:55][C:52]([C:53]#[N:54])=[C:51]([O:57][C@@H:58]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH2:59][CH2:60][CH2:61]NC)[CH:50]=1>O1CCCC1.C1(C)C=CC=CC=1>[Cl:48][C:49]1[CH:56]=[CH:55][C:52]([C:53]#[N:54])=[C:51]([O:57][C@@H:58]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH2:59][CH2:60][CH2:61][Cl:32])[CH:50]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 34427894-Chloro-2-hydroxybenzonitrileHCID 865883464-Chloro-2-[[(1R)-4-(methylamino)-1-phenylbutyl]oxy]benzonitrile ethanedioate

Product 1

HCID 698293454-Chloro-2-[[(1r)-4-chloro-1-phenylbutyl]oxy]benzonitrileYield 197.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.86 g) was added dropwise to a solution of triphenylphosphine (2.81 g), 4-chloro-2-hydroxybenzonitrile (1.49 g) and the product from step (a) (1.79 g) in tetrahydrofuran (5 ml) and toluene (60 ml) at 0° C. and stirred at 0° C. for 4hand at 20° C. for 18 h. The solvent was removed in vacuo and the residue was purified by chromatography on silica eluting with hexane-diethyl ether (4:1) to give the title compound as a colourless oil (2.80 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography on silica eluting with hexane-diethyl ether (4:1)

Sources & evidence

ORD record
ord-ff1ee18df3204078b4bad0be70063c05
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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