Hydrochloric Acid → HCID 57826058, compound

HRID 1405931Notes

Reaction equation

HRID 1405931 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]1([C:27]2[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=2)([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17]1.N1C=CC=CC=1.Cl>CC#N>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:30]1[CH:29]=[CH:28][C:27]([C:16]2([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)[CH2:19][CH2:18][CH2:17]2)=[CH:32][CH:31]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 14251338HCID 14251338, compound

Product 1

HCID 57826058HCID 57826058, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.350 mL) was added to a solution of 4,4′-(cyclobutane-1,1-diyl)diphenol (500 mg) and pyridine (0.505 mL) in MeCN (10 mL) at 0° C. The mixture was stirred at room temperature for 40 min. The mixture was neutralized with 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 4-[1-(4-hydroxyphenyl)cyclobutyl]phenyl trifluoromethanesulfonate (160 mg) as colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-65e2e3bbec77439d9206a88059f31434
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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