Triphenylphosphine → 3-Ethoxycarbonyl-1,1,1-triphenyl-6-(4-ethylphenyl)-2-aza-1lambda5-phosphahexa-1,3,5-triene

HRID 12536Notes

Reaction equation

HRID 12536 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:20](/[C:23](=[CH:29]\[CH:30]=[CH:31]\[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH3:39])=[CH:34][CH:33]=1)/[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N+]=[N-]>C(OCC)C>[CH2:27]([O:26][C:24]([C:23](=[CH:29][CH:30]=[CH:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][CH3:39])=[CH:36][CH:37]=1)[N:20]=[P:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:25])[CH3:28]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86619070ethyl (2Z,4E)-2-azido-5-(4-ethylphenyl)penta-2,4-dienoate2×

Product 1

HCID 866190693-Ethoxycarbonyl-1,1,1-triphenyl-6-(4-ethylphenyl)-2-aza-1lambda5-phosphahexa-1,3,5-triene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

General Procedure J. A solution of triphenylphosphine (1.2 g, 4.54 mmol) in diethyl ether (10 ml) was added dropwise to a solution of ethyl (2Z,4E)-2-azido-5-(4-ethylphenyl)penta-2,4-dienoate (Compound 44, 1.2 g, 4.54 mmol) in diethyl ether (20 ml) at 0° C. The solution was stirred for 12 hours at room temperature. Evaporation of solvent afforded a crude yellow solid, which was purified by column chromatography (silica gel, 20% ethyl acetate in hexane) to give the title compound.

Workup

  1. customEvaporation of solvent
  2. customafforded a crude yellow solid, which
  3. customwas purified by column chromatography (silica gel, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a6ee2b9eb8ae41b1997326c72ac4001b
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Reaction notes

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