Sodium Thiosulfate → Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)

HRID 1602571Notes

Reaction equation

HRID 1602571 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:6]1([C@@H:4]2[CH2:5][C@H:3]2[CH:2]=[O:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 1561175(2-phenylcyclopropyl)methanol

Product 1

HCID 12323031Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)Yield 50.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

104 mg of the alcohol was dissolved in 5 ml of chloroform and stirred with 445 mg of the Dess-Martin reagent (periodinane) at room temperature for 30 minutes. The reaction solution was poured into a mixture of saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1] to give 52 mg of the title compound as a colorless oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1]

Sources & evidence

ORD record
ord-ad075589ec584c1a8818aa1c1416644c
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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