Triphenylphosphine → HCID 58903114, compound

HRID 273398Notes

Reaction equation

HRID 273398 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:20]=[C:19]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:18]=[C:17]([CH3:28])[C:16]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35]O)[CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:28][C:17]1[CH:18]=[C:19]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:20]=[C:15]([CH3:14])[C:16]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)[CH:30]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58903129HCID 58903129, compound

Product 1

HCID 58903114HCID 58903114, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (3.28 g, 18.2 mmol), [2′,6′-dimethyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methanol (5.15 g, 16.5 mmol) and triphenylphosphine (5.63 g, 21.5 mmol) in tetrahydrofuran (100 mL) was added dropwise diethyl azodicarboxylate (40% toluene solution, 9.7 mL) at 0° C. with stirring, and the mixture was stirred at room temperature for 48 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1) to give the title compound (2.92 g, yield 37%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 48 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-d083326ab2d94deaa8f4173961b9a5ce
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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