Hydrochloric Acid → Ethyl 4'-(2-methanesulfonyloxyethoxy)biphenyl-4-carboxylate

HRID 30773Notes

Reaction equation

HRID 30773 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.C(N(CC)CC)C.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][S:2]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 23090738Ethyl 4'-(2-hydroxyethoxy)biphenyl-4-carboxylate

Product 1

HCID 23090736Ethyl 4'-(2-methanesulfonyloxyethoxy)biphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.13 mL) was added to an ice-cooled mixture of ethyl 4′-(2-hydroxyethoxy)biphenyl-4-carboxylate (0.41 g) and triethylamine (0.30 mL) in tetrahydrofuran (8 mL) with stirring. The mixture was stirred at that temperature for 30 min, at room temperature for 45 min, and at 45° C. for 1 hr. Methanesulfonyl chloride (0.13 mL) and triethylamine (0.30 mL) were added every an hour to the reaction mixture for 3 times at 45° C., and the mixture was stirred at 70° C. for 3 hrs. 1 mol/L hydrochloric acid and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford ethyl 4′-(2-methanesulfonyloxyethoxy)biphenyl-4-carboxylate (0.32 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at that temperature for 30 min, at room temperature for 45 min
  3. stirringthe mixture was stirred at 70° C. for 3 hrs
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b377c46e9f4246e7a7ba78254306f04c
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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