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

HRID 971285
Notes
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Reaction equation

HRID 971285 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23994
Zinc
Catalyst
HCID 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-c57e2f6dc16f42158a6d43e2eb244af5
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07312359B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes