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

HRID 1392646
Notes
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Reaction equation

HRID 1392646 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-7524c919d5414fcc93309a0cfa05c5eb
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07342115B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes