Triacetoxyperiodinane → 1433407-08-9

HRID 2283429Notes

Reaction equation

HRID 2283429 reaction equation
[OH:1][CH2:2][C:3]1([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5][CH2:4]1.C(=O)([O-])O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:4][CH2:5]1)=[O:1]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 680062131268842-81-4

Product 1

HCID 575354611433407-08-9

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 To a stirred suspension of tert-butyl 1-(hydroxymethyl)cyclopropane-1-carboxylate (0.16 g, 0.929 mmol) and sodium hydrogen carbonate (0.312 g, 3.72 mmol) in DCM (5.57 mL) at room temperature was added Dess-Martin periodinane (0.788 g, 1.86 mmol). The mixture was stirred at room temperature for 1 hour before it was quenched by the addition of a 1:1 mixture of saturated NaHCO3 solution and saturated Na2S2O3 solution. After stirring for an additional 1 hour the phases were separated and the aqueous phase was extracted into DCM (×2). Combined organic extracts were dried (Na2SO4), filtered and concentrated giving tert-butyl 1-formylcyclopropane-1-carboxylate which was used without further purification, 0.141 g.

Workup

  1. customwas quenched by the addition of a 1:1 mixture of saturated NaHCO3 solution and saturated Na2S2O3 solution
  2. stirringAfter stirring for an additional 1 hour the phases
  3. customwere separated
  4. extractionthe aqueous phase was extracted into DCM (×2)
  5. dry with materialCombined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-41edf6f12eec43c7b644e7e0e77aa7d3
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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