(3-Bromopropyl)benzene → 2-(3-Methyl-1H-benzo[b]thiophen-2-yl)-5-phenylpentanoic Acid

HRID 382446Notes

Reaction equation

HRID 382446 reaction equation
[CH3:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[CH2:7][C:8]([OH:10])=[O:9].C([Li])CCC.Br[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>C1COCC1.O>[CH3:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[CH:7]([CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:8]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 12503(3-Bromopropyl)benzeneHCID 14798Sodium HydroxideHCID 27798673-Methylbenzo[b]thiophene-2-acetic acidHCID 178418339Butyllithium

Product 1

HCID 99272812-(3-Methyl-1H-benzo[b]thiophen-2-yl)-5-phenylpentanoic AcidYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-methylbenzo[b]thiophene-2-acetic acid (1.00 g) in THF at −78° C. under nitrogen was added a solution of n-butyllithium in hexanes (2.5M; 3.98 ml). Stirring was continued for 15 mins at this temperature before 1-bromo-3-phenylpropane (965 mg) was added. The mixture was stirred for 30 mins before allowing to warm up to RT and then stirred at RT for a further 1 h. The reaction mixture was poured on to a mixture of water (50 ml) and 1 N sodium hydroxide solution (10 ml). The organic layer was separated and washed with water (2×10 ml), brine (10 ml) and dried (MgSO4). Filtration and evaporation of solvents under reduced pressure gaven the crude product, which was purificatied by silica gel column chromatography, eluting with 2:1 hexane/ethyl acetate, to give the title compound (579 mg, 37%) as a pale green oil. Rf 0.45 (2:1 hexane/ethyl acetate).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 30 mins
  3. stirringstirred at RT for a further 1 h
  4. customThe organic layer was separated
  5. washwashed with water (2×10 ml), brine (10 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation of solvents under reduced pressure gaven the crude product, which
  8. washeluting with 2:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-36593c746b624515add7a70523aa0c4a
Source dataset
uspto-grants-2001_10
Patent number
US06310088B1

Reaction notes

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