Triacetoxyperiodinane → HCID 86714671, compound

HRID 1409461Notes

Reaction equation

HRID 1409461 reaction equation
[OH:1][CH:2]([C:4]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:6][N:5]=1)[CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:2]([C:4]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:6][N:5]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86714670HCID 86714670, compound

Product 1

HCID 86714671HCID 86714671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a flask containing ethyl 3-(1-hydroxyethyl)-1,2,4-oxadiazole-5-carboxylate (53.7 mmol, 10 g) in DCM (100 ml), Dess-Martin periodinane (80 mmol, 34.2 g) was added at 0° C. in portions and the resulting mixture was stirred at RT for 16 h. The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with DCM. The organic layers were dried, filtered and evaporated. The product was purified by flash-chromatography. Yield 9.12 g. 1H-NMR (400 MHz; CDCl3): δ 1.47 (t, 3H), 2.76 (s, 3H), 4.58 (q, 2H).

Workup

  1. additionwas added at 0° C. in portions
  2. customThe reaction mixture was quenched with aqueous NaHCO3 solution
  3. extractionextracted with DCM
  4. customThe organic layers were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-d85060183b77497d86067d3a3947e62c
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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