Benzene → (6-Benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester

HRID 339182Notes

Reaction equation

HRID 339182 reaction equation
C1C=CC=CC=1.II.[C:9]1([S:15]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[CH2:23][CH2:22][CH2:21]3)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[CH:30](C)[C:31]([O:33][CH2:34]C)=[O:32]>O.[Zn]>[CH3:34][O:33][C:31](=[O:32])[CH2:30][C:24]1([OH:28])[C:25]2[C:20](=[CH:19][C:18]([S:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)(=[O:17])=[O:16])=[CH:27][CH:26]=2)[CH2:21][CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 807IodineHCID 79040Ethyl 2-bromopropionateHCID 590217396-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 66651224(6-Benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A solution/suspension of anhydrous benzene (25 mL), powdered Zinc metal (0.505 g, 7.72 mmol), I2 (0.01 g) and 6-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one was stirred for 10 minutes at room temperature. Ethyl bromopropionate (0.784 mL, 1.18 g, 7.07 mmol) was added and the reaction mixture was heated to reflux for 2.5 hours. The reaction mixture was allowed to cool, diluted with 300 mL of water and extracted twice with 250 mL of EtOAc. The combined organic layers were washed with water and saturated brine, dried (MgSO4) and evaporated under reduced pressure to yield (6-benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester. MS: 375 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. temperatureto cool
  4. extractionextracted twice with 250 mL of EtOAc
  5. washThe combined organic layers were washed with water and saturated brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2a0393b549ba458b91456fa8f4dbc7dc
Source dataset
uspto-grants-2014_11
Patent number
US08889906B2

Reaction notes

Loading…