Methanol → 2-[4-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-methyl-1,2-oxazol-5-yl]acetic acid

HRID 922246Notes

Reaction equation

HRID 922246 reaction equation
O1CCCC1.[CH3:6][O:7]/[N:8]=[C:9](/[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)\[CH2:10][O:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]([CH3:34])=[N:26][O:27][C:28]=3[CH2:29][C:30]([O:32]C)=[O:31])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.CO.[OH-].[Li+]>O>[CH3:6][O:7]/[N:8]=[C:9](/[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)\[CH2:10][O:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[C:25]([CH3:34])=[N:26][O:27][C:28]=3[CH2:29][C:30]([OH:32])=[O:31])=[CH:22][CH:23]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 88581611methyl 2-[4-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-methyl-1,2-oxazol-5-yl]acetate

Product 1

HCID 566405092-[4-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-methyl-1,2-oxazol-5-yl]acetic acidYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged with tetrahydrofuran (5 mL). To the stirred solvent were added Methyl (4-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}-3-methyl-1,2-oxazol-5-yl)acetate (0.47 g, 0.94 mmol), methanol (3 mL) and lithium hydroxide (0.07 g, 0.94 mmol) in water (3 mL). After addition, the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to distill off the solvent; the crude was washed with diethyl ether (5 mL). Water (1 mL) was added and the aqueous layer was acidified with saturated citric acid solution to make pH 6. The aqueous layer was extracted with ethyl acetate (5 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as white solid (0.32 g, yield: 70.2%).

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. additionAfter addition
  3. concentrationThe reaction mixture was concentrated
  4. distillationto distill off the solvent
  5. washthe crude was washed with diethyl ether (5 mL)
  6. additionWater (1 mL) was added
  7. extractionThe aqueous layer was extracted with ethyl acetate (5 mL)
  8. dry with materialThe organic layer was dried over anhydrous Na2SO4
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ebc35b8d75fd4f89bf206071e4816586
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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