Triphenylphosphine → (S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

HRID 1845893Notes

Reaction equation

HRID 1845893 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([OH:12])[CH3:11].[N+:13]([C:16]1[C:21](O)=[CH:20][CH:19]=[CH:18][N:17]=1)([O-:15])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@@H:10]([O:12][C:21]1[C:16]([N+:13]([O-:15])=[O:14])=[N:17][CH:18]=[CH:19][CH:20]=1)[CH3:11]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 270573-Hydroxy-2-nitropyridineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11344814(R)-1-(2,6-dichloro-3-fluorophenyl)ethanol

Product 1

HCID 86327669(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (R)-1-(2,6-dichloro-3-fluorophenyl)ethanol (12 g, 57.42 mmol) was dissolved in tetrahydrofuran (110 mL), 2-nitro-3-hydroxypyridine (8.84 g, 63.16 mmol) and triphenylphosphine (21.06 g, 80.39 mmol) were added, and the reaction mixture was stirred for 1 h at room temperature. Diisopropyl azodicarboxylate (16.26 g, 80.39 m mol) was added dropwise under the cooling of ice bath. The temperature of the reaction liquid was raised to 30° C., and the reaction was stirred overnight. After TLC test has showed that reaction was completed, the reaction liquid was concentrated under reduced pressure;

Workup

  1. temperaturecooling of ice bath
  2. customThe temperature of the reaction liquid
  3. temperaturewas raised to 30° C.
  4. stirringthe reaction was stirred overnight
  5. customAfter TLC test has showed that reaction
  6. customthe reaction liquid
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-39ed635b119a4c2984d5eeded2240137
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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