Tributylphosphine → Methyl (4'-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetate

HRID 2076588Notes

Reaction equation

HRID 2076588 reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[CH3:32][O:33][CH:34]([O:51][CH3:52])[C:35]1[C:40]([O:41][CH2:42][O:43][CH3:44])=[C:39]([C:45]([F:48])([F:47])[F:46])[CH:38]=[CH:37][C:36]=1[CH2:49][OH:50].O[C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][C:63]([CH2:66][C:67]([O:69][CH3:70])=[O:68])=[CH:62][CH:61]=2)=[CH:56][CH:55]=1>O1CCCC1>[CH3:52][O:51][CH:34]([O:33][CH3:32])[C:35]1[C:40]([O:41][CH2:42][O:43][CH3:44])=[C:39]([C:45]([F:46])([F:47])[F:48])[CH:38]=[CH:37][C:36]=1[CH2:49][O:50][C:54]1[CH:55]=[CH:56][C:57]([C:60]2[CH:65]=[CH:64][C:63]([CH2:66][C:67]([O:69][CH3:70])=[O:68])=[CH:62][CH:61]=2)=[CH:58][CH:59]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 67119352[2-(Dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)phenyl]methanolHCID 86088038Methyl (4'-hydroxy-1,1'-biphenyl-4-yl)acetate

Product 1

HCID 86617395Methyl (4'-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetateYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-(Azodicarbonyl)dipiperidine (3.10 g, 12.3 mmol) and tri-n-butylphosphine (3.10 ml, 12.4 mmol) were successively added to a solution of [2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)phenyl]methanol (3.20 g, 10.3 mmol) obtained in Example (6-6) and methyl (4′-hydroxy-1,1′-biphenyl-4-yl)acetate (2.50 g, 10.3 mmol) obtained in Example (6-2) in tetrahydrofuran (40 ml) and the mixture was stirred at room temperature for 5 hours. After the formed white precipitate was removed by filtration, the precipitate was washed with ethyl acetate. After the filtrate was poured into water and the mixture was extracted with ethyl acetate (three times), the organic layer was successively washed with a 3N aqueous sodium hydroxide solution, water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1) to give methyl (4′-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (3.16 g, yield: 58%).

Workup

  1. customAfter the formed white precipitate was removed by filtration
  2. washthe precipitate was washed with ethyl acetate
  3. additionAfter the filtrate was poured into water
  4. extractionthe mixture was extracted with ethyl acetate (three times)
  5. washthe organic layer was successively washed with a 3N aqueous sodium hydroxide solution, water
  6. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-6d3a02313691443bb5bcaaaaf92ad817
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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