Tetrahydrofuran → Phenyl(8-thiabicyclo[3.2.1]oct-3-yl)methanone

HRID 900765Notes

Reaction equation

HRID 900765 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]12[S:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][CH:11]([C:17]#N)[CH2:10]2.C1C[O:22]CC1>>[C:1]1([C:17]([CH:11]2[CH2:12][CH:13]3[S:16][CH:9]([CH2:15][CH2:14]3)[CH2:10]2)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 692908968-Thiabicyclo[3.2.1]octane-3-carbonitrileHCID 178418255HCID 178418255, compound

Product 1

HCID 69290822Phenyl(8-thiabicyclo[3.2.1]oct-3-yl)methanoneYield 38%

Procedure

A 3M etheral solution of phenyl magnesium bromide (6.72 ml, 20.16 mmol) was added at 0° C. to a solution of the above nitrile (1.03 g, 6.72 mmol) in dry THF (10 ml). After 30 minutes, the ice bath was removed and the reaction continued at room temperature for 16 hours. The reaction was carefully quenched by addition of a saturated aqueous NH4Cl solution. After addition of ether, organic layer was separated, washed with brine, dried over MgSO4 and concentrated. The residual oil was chromatographied on silica gel (hexane/AcOEt 94/6) to give the phenyl(8-thiabicyclo[3.2.1]oct-3-yl)methanone 22 as a colorless oil (586 mg, 38%).

Workup

  1. customthe ice bath was removed
  2. waitthe reaction continued at room temperature for 16 hours
  3. customThe reaction was carefully quenched by addition of a saturated aqueous NH4Cl solution
  4. additionAfter addition of ether, organic layer
  5. customwas separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ee9570609fa24743980c2785cc4347bf
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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