Water → Benzyl 4'-(2-methanesulfonyloxy-ethoxy)-3'5'-dimethylbiphenyl-4-carboxylate

HRID 2243543Notes

Reaction equation

HRID 2243543 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[CH:19][CH:18]=2)=[CH:12][C:11]=1[CH3:33].C(N(CC)CC)C.O>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][S:2]([O:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH3:33])=[CH:12][C:13]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])=[CH:19][CH:18]=2)=[CH:14][C:15]=1[CH3:16])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23090745Benzyl 4'-(2-hydroxyethoxy)-3',5'-dimethylbiphenyl-4-carboxylate

Product 1

HCID 23090786Benzyl 4'-(2-methanesulfonyloxy-ethoxy)-3'5'-dimethylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.10 mL) was added to an ice-cooled mixture of benzyl 4′-(2-hydroxy-ethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate (0.38 g) and triethylamine (0.21 mL) in methylene chloride (5 mL) with stirring, and the mixture was stirred at room temperature for 1 hr. Water 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 benzyl 4′-(2-methanesulfonyloxy -ethoxy)-3′5′-dimethylbiphenyl-4-carboxylate (0.45 g).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f420e5c56cee4f16b7465ad1868bfa1e
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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