4-Bromothioanisole → 5,5-Dimethyl-1-(4-(methylthio)phenyl)-2-phenylcyclopent-2-enol

HRID 325189Notes

Reaction equation

HRID 325189 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li]CCCC.[CH3:15][C:16]1([CH3:28])[C:20](=[O:21])[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH2:17]1>C1COCC1>[CH3:15][C:16]1([CH3:28])[C:20]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=2)([OH:21])[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH2:17]1

Participants

5

Reactant 3

HCID 660374-BromothioanisoleHCID 125706695,5-Dimethyl-2-phenylcyclopent-2-en-1-oneHCID 178418339Butyllithium

Product 1

HCID 220026325,5-Dimethyl-1-(4-(methylthio)phenyl)-2-phenylcyclopent-2-enolYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of p-bromothioanisole (5 g) in 100 mL of THF was added a solution n-BuLi (10 mL, 2.5 M in hexane). After stirring for 45 min. at −78° C., a solution of the product of Step 3 (2.4 g) in 10 mL of THF was added dropwise. The reaction mixture was stirred for 10 min. and then quenched with 100 mL of saturated solution of NH4Cl. The product was extracted with 300 mL of 2:1 hexanes/EtOAc. The extract was dried over Na2SO4 and concentrated. Th e residue was purified by chromatography eluting with 10:1 hexane/EtOAc to give 3.5 g of the title compound.

Workup

  1. stirringThe reaction mixture was stirred for 10 min.
  2. customquenched with 100 mL of saturated solution of NH4Cl
  3. extractionThe product was extracted with 300 mL of 2:1 hexanes/EtOAc
  4. dry with materialThe extract was dried over Na2SO4
  5. concentrationconcentrated
  6. customTh e residue was purified by chromatography
  7. washeluting with 10:1 hexane/EtOAc

Sources & evidence

ORD record
ord-021e66a0153e478e8016220924a2ef60
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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