Water → Ethyl [4'-(2-methanesulfonyloxy-ethoxy)-2',6'-dimethylbiphenyl-4-yloxy]acetate

HRID 30767Notes

Reaction equation

HRID 30767 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=2)=[C:12]([CH3:30])[CH:11]=1.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[CH:15]=[C:14]([CH3:16])[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=2)=[C:12]([CH3:30])[CH:11]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86605508HCID 86605508, compound

Product 1

HCID 86605507Ethyl [4'-(2-methanesulfonyloxy-ethoxy)-2',6'-dimethylbiphenyl-4-yloxy]acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.17 mL) was added to an ice-cooled mixture of ethyl [4′-(2-hydroxyethoxy)-2′,6′-dimethylbiphenyl-4-yloxy]acetate (0.58 g) and triethylamine (0.36 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 ethyl [4′-(2-methanesulfonyloxyethoxy)-2′,6′-dimethylbiphenyl-4-yloxy]acetate.

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-3f759c24098a474d8fb6302bb0a88844
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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