Triacetoxyperiodinane → HCID 57868840, compound

HRID 1966139Notes

Reaction equation

HRID 1966139 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-7b187145f4b240679c924090932682bf
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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