Cyclobutanone → (1,1'-Bicyclobutyl)-1,1'-diol

HRID 2070614Notes

Reaction equation

HRID 2070614 reaction equation
[Cl-].[Li+].[I-].[Sm+2].[I-].[C:6]1(=[O:10])[CH2:9][CH2:8][CH2:7]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[C:6]1([OH:10])([C:6]2([OH:10])[CH2:9][CH2:8][CH2:7]2)[CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 14496CyclobutanoneHCID 24477Sodium ThiosulfateHCID 433294Lithium ChlorideHCID 178506586HCID 178506586, compound

Product 1

HCID 265811(1,1'-Bicyclobutyl)-1,1'-diolYield 47.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium chloride (2.12 g) in tetrahydrofuran (60 mL) was added samarium(II) iodide (5.0 g) under argon atmosphere, followed by stirring the mixture at room temperature for 15 minutes. To this reaction mixture was added dropwise a solution of cyclobutanone (825 mg) in tetrahydrofuran (5 mL), followed by stirring the mixture at room temperature for 1 hour. To the reaction mixture was added saturated aqueous sodium thiosulfate solution under ice-cooling, followed by extraction with diethyl ether three times. The organic layers were combined, washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 3:2) to give bicyclobutyl-1,1′-diol (399 mg).

Workup

  1. stirringby stirring the mixture at room temperature for 1 hour
  2. temperaturecooling
  3. extractionfollowed by extraction with diethyl ether three times
  4. washwashed with saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 3:2)

Sources & evidence

ORD record
ord-db63db9727194a4dadd38762fc4ae094
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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