Water → (6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-acetic acid ethyl ester

HRID 2103343Notes

Reaction equation

HRID 2103343 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([OH:20])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][O:20][CH:16]1[C:17]2[C:12](=[CH:11][C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])=[CH:19][CH:18]=2)[CH2:13][CH2:14][CH2:15]1)[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 575267796-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ol

Product 1

HCID 57804256(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-acetic acid ethyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ol (1.2 g, 4.16 mmol) was dissolved in 60 mL of dry DMF, and the reaction mixture was cooled in an ice bath. Sodium hydride (0.2 g of 60% solid in oil, washed with hexanes) was added, and the reaction mixture was stirred under nitrogen for 20 minutes. Ethyl bromoacetate (0.55 mL) was added dropwise, and stirring was continued for three hours, during which time the reaction mixture was allowed to warm to room temperature. Water (250 mL) was added to the reaction mixture, and the aqueous mixture was extracted twice with 150 mL of EtOAc. The combined organic layers were washed with water, brine, dried over MgSO4, and the solvent was removed under reduced pressure to yield an oil which was eluted through silica gel under medium pressure with 4:1 EtOAc/hexanes. Removal of solvent under reduced pressure afforded 0.75 g (2.0 mmol, 48%) of (6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-acetic acid ethyl ester as an oil. MS: 375 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. stirringstirring
  3. waitwas continued for three hours, during which time
  4. extractionthe aqueous mixture was extracted twice with 150 mL of EtOAc
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed under reduced pressure
  8. customto yield an oil which
  9. washwas eluted through silica gel under medium pressure with 4:1 EtOAc/hexanes
  10. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-608ef455aeb5493d87b0382180c2faef
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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