Hydrochloric Acid → 3-(3-(((2-(2,2-Dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoic acid

HRID 1049420Notes

Reaction equation

HRID 1049420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([CH2:24][CH2:25][CH:26]=[O:27])[CH:21]=[CH:22][CH:23]=2)=[CH:12][C:11]=1[CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30].P([O-])(O)(O)=[O:34].[Na+].Cl([O-])=O.[Na+].CC(=CC)C.Cl>C(O)(C)(C)C.O>[CH3:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:11]1[CH:12]=[C:13]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([CH2:24][CH2:25][C:26]([OH:34])=[O:27])[CH:21]=[CH:22][CH:23]=2)[CH:14]=[CH:15][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 1177600203-(3-(((2'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)oxy)methyl)phenyl)propanal

Product 1

HCID 1177599763-(3-(((2-(2,2-Dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoic acidYield 83.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a solution of 3-(3-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)propanal (152 mg) in tert-butanol (3.5 mL) were successively added water (0.50 mL), sodium dihydrogen phosphate (126 mg), sodium chlorite (95 mg) and 2-methyl-2-butene (0.19 mL), and the mixture was stirred at room temperature for 45 min. 1N Hydrochloric acid and water were added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (132 mg) as a colorless oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-28d8a966863947ea9b4fa09e6cfd5339
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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