Hexane → HCID 22002640, compound

HRID 325185Notes

Reaction equation

HRID 325185 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH3:21][C:22]1([CH3:34])[CH2:26][C:25](=[O:27])[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:23]1>C1COCC1>[CH3:21][C:22]1([CH3:34])[CH2:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=2)([OH:27])[C:24]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:23]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 660374-BromothioanisoleHCID 22002654HCID 22002654, compoundHCID 178418339Butyllithium

Product 1

HCID 22002640HCID 22002640, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromothioanisole (2.51 g, 12.3 mmol) in THF (20 mL) at −78° C. was added dropwise a solution of 2.5 M n-butyl lithium in hexane (4.8 mL, 12.0 mmol). The resulting suspension was stirred at this temperature for 1 h and then a solution of 4,4-dimethyl-2-phenyl-2-cyclopenten-1-one from Step 2 (1.25 g, 6.7 mmol) in THF (20 mL) was added slowly via cannula to the cold reaction. The reaction was stirred for 15 min at −78° C. and then for 30 min. at r.t. The reaction was stopped by dilution with NH4OAc buffer 25% w/v and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography eluting with 10% EtOAc/hexanes to give the title compound as a colorless gum.

Workup

  1. stirringThe reaction was stirred for 15 min at −78° C.
  2. waitfor 30 min. at r.t
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography
  7. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-853df2e9017e4ac0a25a780c8055c0b7
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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