Hydrochloric Acid → 1-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2-methylpropan-1-one

HRID 1049606Notes

Reaction equation

HRID 1049606 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:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[CH:26]([OH:30])[CH:27]([CH3:29])[CH3:28].C(N(CC)CC)C.Cl>CS(C)=O>[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:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:26](=[O:30])[CH:27]([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 117760124HCID 117760124, compound

Product 1

HCID 1177599061-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2-methylpropan-1-oneYield 84.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)-2-methylpropan-1-ol (256.9 mg) in DMSO (4.2 mL) were added triethylamine (523 μL) and sulfur trioxide pyridine complex (299 mg) at room temperature, and the mixture was stirred for 24 hr. To the reaction mixture was added 0.5N hydrochloric acid, and the 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 (217 mg) as a pale-yellow oil.

Workup

  1. extractionthe 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-6c09529d27f142e2aadffab83ce805c2
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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