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Triphenylphosphine → 2-(2,6-Diethyl-phenyl)-5-[1-(3-ethoxy-phenoxy)-butyl]4-ethoxy-pyridine

HRID 251615
Notes
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Reaction equation

HRID 251615 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[CH:15][C:14]([CH:17]([OH:21])[CH2:18][CH2:19][CH3:20])=[C:13]([O:22][CH2:23][CH3:24])[CH:12]=1)[CH3:2].[CH2:25]([O:27][C:28]1[CH:29]=[C:30](O)[CH:31]=[CH:32][CH:33]=1)[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[NH4+].[Cl-]>C1COCC1.CCCCCC>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]([O:22][CH2:23][CH3:24])[C:14]([CH:17]([O:21][C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([O:27][CH2:25][CH3:26])[CH:33]=2)[CH2:18][CH2:19][CH3:20])=[CH:15][N:16]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 693063-EthoxyphenolHCID 5462977Diethyl azodicarboxylateHCID 596783161-[6-(2,6-Diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butan-1-ol

Product 1

HCID 59678259
2-(2,6-Diethyl-phenyl)-5-[1-(3-ethoxy-phenoxy)-butyl]4-ethoxy-pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A mixture of 1-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butan-1-ol (67 mg, 0.20 mmol), 3-ethoxy-phenol (34 mg, 0.25 mmol), triphenylphosphine (65 mg, 0.25 mmol), and DEAD (36 mg, 0.25 mmol) in THF (1 mL) is stirred at room temperature overnight. Aqueous NH4Cl solution (5 mL) and hexane (10 mL) are added to the mixture, and the organic layer is separated. The organic layer is washed with NaHCO3 solution, brine, dried over Na2SO4, and concentrated. The residue is purified by PTLC to give 2-(2,6-diethyl-phenyl)-5-[1-(3-ethoxy-phenoxy)-butyl]-4-ethoxy-pyridine. 1H NMR (CDCl3) 8.55 (s, 1H), 7.27 (m, 1H), 7.07-7.14 (m, 3H), 6.73 (s, 1H), 6.43-6.49 (m, 3H), 5.57 (m, 1H), 4.13 (q, 2H), 3.95 (q, 2H), 2.56-2.37 (m, 4H), 1.85-2.05 (m, 2H), 1.40-1.60 (m, 5H), 1.37 (t, 3H), 0.96-1.08 (m, 9H).

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with NaHCO3 solution, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by PTLC

Sources & evidence

ORD record
ord-fe69c923ff9544ceb47288530cde29a0
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863454B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes