Triacetoxyperiodinane → HCID 89825189, compound

HRID 2273854Notes

Reaction equation

HRID 2273854 reaction equation
[CH:1]1([N:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1([N:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22])[C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89825024HCID 89825024, compound

Product 1

HCID 89825189HCID 89825189, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-cyclohexyl-N-(6-hydroxyhexyl)benzamide (136 mg, 0.45 mmol) was dissolved in methylene chloride (6 mL) and treated with Dess-Martin reagent (247.0 mg, 0.58 mmol). The oxidation was finished in 4 hours. The mixture was diluted with methylene chloride and washed with saturated bicarbonate and sodium thiosulfate (5%). The organic phase was concentrated and purified on silica gel with ethyl acetate: hexanes from 0:1 to 2:8 gave the desired product as a clear oil (108.2 mg, 80%). 1H NMR (300 MHz, CDCl3): δ 9.80 (s, 1H), 7.46-7.28 (m, 5H), 3.60-2.98 (m, 3H), 2.60-2.15 (m, 2H), 1.95-0.80 (m, 16H).

Workup

  1. washwashed with saturated bicarbonate and sodium thiosulfate (5%)
  2. concentrationThe organic phase was concentrated
  3. custompurified on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-2628cc081b1b4c54b30c4c8c9539ba0a
Source dataset
uspto-grants-2015_09
Patent number
US09126937B2

Reaction notes

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