Triphenylphosphine → HCID 86641939, compound

HRID 384109Notes

Reaction equation

HRID 384109 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[O:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[CH2:53]O)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:53][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27628652-Bromo-5-hydroxypyridineHCID 36601112-Phenoxybenzyl alcohol

Product 1

HCID 86641939HCID 86641939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromopyridin-3-ol (1.76 g) in tetrahydrofuran (20 ml), 3.20 g of triphenylphosphine, 5.52 ml of diethyl azodicarboxylate (45% toluene solution) and 2.43 g of (2-phenoxyphenyl)methanol were added, and the reaction solution was stirred overnight at room temperature. The reaction solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-15:85)) to afford the title compound as a yellow oil.

Workup

  1. distillationThe reaction solvent was distilled off under reduced pressure
  2. customthe residue obtained
  3. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-15:85))

Sources & evidence

ORD record
ord-a6bb457da661413a8ea1867335fcd100
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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