Tributylphosphine → HCID 59364071, compound

HRID 1691520Notes

Reaction equation

HRID 1691520 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH2:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]O)[CH:28]=2)=[C:22]([CH3:35])[CH:21]=1)[CH3:15].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH2:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][O:1][C:2]3[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=3)[CH:28]=2)=[C:22]([CH3:35])[CH:21]=1)[CH3:15]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 5319562Methyl-P-CoumarateHCID 23111752[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methanol

Product 1

HCID 59364071HCID 59364071, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of methyl (2E)-3-(4-hydroxyphenyl)acrylate (0.713 g, 4.00 mmol), [4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methanol (1.20 g, 4.00 mmol) and tributylphosphine (1.29 g, 6.40 mmol) in toluene (65 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (1.61 g, 6.40 mmol) was added in small portions, and the mixture was stirred at room temperature for 24 hr. Hexane (35 mL) was added to the reaction mixture. The precipitated insoluble material was filtrated, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75), and recrystallized from ethyl acetate-hexane to give the title compound (1.58 g, yield 86%) as colorless crystals.

Workup

  1. filtrationThe precipitated insoluble material was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3bd7a0c6badd4ed09e6c7e6464d0466e
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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