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Triphenylphosphine → HCID 23083008, compound

HRID 2422293
Notes
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Reaction equation

HRID 2422293 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:16]=1[O:17][C:18]1[CH:19]=[C:20]([CH2:24]O)[CH:21]=[CH:22][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:14][C:15]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:16]=1[O:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 230831353-(2,6-Dimethylphenoxy)benzenemethanolHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 23083008HCID 23083008, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (0.25 g, 1.39 mmol), [3-(2,6-dimethylphenoxy)phenyl]methanol (0.41 g, 1.81 mmol) and triphenylphosphine (0.47 g, 1.81 mmol) in tetrahydrofuran (5 mL) was added dropwise diethyl azodicarboxylate toluene solution (40%, 0.82 mL) with stirring at 0° C., and the mixture was stirred at room temperature for 16 hrs. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1) to give the title compound (0.27 g, yield 50%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-f59fe26f325a40f18515e2fe2df45674
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960369B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes