Triacetoxyperiodinane → HCID 44128631, compound

HRID 512000Notes

Reaction equation

HRID 512000 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:16]1[O:17][C:18]([CH3:21])=[N:19][N:20]=1)[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[O:17][C:18]([CH3:21])=[N:19][N:20]=1)=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66930888HCID 66930888, compound

Product 1

HCID 44128631HCID 44128631, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 64.1 (64 mg, 0.22 mmol) in wet methylene chloride (5 mL) at room temperature, under nitrogen was added Dess-Martin periodinane (140 mg, 0.33 mmol) and the resulting suspension stirred for 2 hours. The reaction mixture was diluted with Na2S2O3 (10% in H2O) and saturated aqueous NaHCO3 solution and the organic phase was separated. The aqueous layer was extracted with AcOEt and the combined organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (50% ethyl acetate-hexane) to give 65.1 (52 mg, 82% yield) as a white solid (m p 75-77° C.).

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous layer was extracted with AcOEt
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by flash column chromatography on silica gel (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1e18700b1e37407b8f93f653822486c3
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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