Triacetoxyperiodinane → HCID 57868840, compound

HRID 1692907Notes

Reaction equation

HRID 1692907 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[CH2:9][CH:8]([OH:10])[CH2:7]2)=[N:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[CH2:9][C:8](=[O:10])[CH2:7]2)=[N:2]1

Participants

6

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57868863HCID 57868863, compound

Product 1

HCID 57868840HCID 57868840, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Isoxazol-3-ylcyclobutanol (0.316 g, 2.27 mmol), as a mixture of cis- and trans-isomers, was dissolved in methylene chloride (10 mL) and Dess-Martin periodinane (0.96 g, 2.3 mmol) was added. After stirring for 2 hours, satd. NaHCO3 solution and brine were added, and the mixture was extracted with three portions of ethyl acetate. The combined extracts were dried over sodium sulfate, decanted and concentrated. Flash column chromatography, eluting with a gradient of 20-50% ethyl acetate in hexanes, afforded product (258 mg, 83%).

Workup

  1. extractionthe mixture was extracted with three portions of ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated
  5. washFlash column chromatography, eluting with a gradient of 20-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8a45cfeaa21f43d18d2af66d7694f785
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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