Triacetoxyperiodinane → HCID 67271267, compound

HRID 225423Notes

Reaction equation

HRID 225423 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[OH:23][CH:24]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH:40]([O:41][CH2:42][C:43]3[S:47][C:46]([C:48]([O:50][CH3:51])=[O:49])=[CH:45][CH:44]=3)[CH2:39][CH2:38][S:37]2(=[O:53])=[O:52])=[CH:32][CH:31]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl>[C:24]([C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH:40]([O:41][CH2:42][C:43]3[S:47][C:46]([C:48]([O:50][CH3:51])=[O:49])=[CH:45][CH:44]=3)[CH2:39][CH2:38][S:37]2(=[O:53])=[O:52])=[CH:34][CH:35]=1)(=[O:23])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67271299HCID 67271299, compound

Product 1

HCID 67271267HCID 67271267, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (44 mg, 0.104 mmol) was added to a solution of the alcohol 14 (42 mg, 0.087 mmol) in CH2Cl2 (2 mL) at 23° C. After stirring for 16 h the reaction mixture with CH2Cl2 and filtered. The filtrate was concentrated in vacuo and purification of the residue by flash column chromatography (silica gel, 1:1 hex/EtOAc) gave 41 mg (98%) of the ketone 16.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo and purification of the residue by flash column chromatography (silica gel, 1:1 hex/EtOAc)

Sources & evidence

ORD record
ord-8ff353b74e004a86b005725840377b82
Source dataset
uspto-grants-2009_07
Patent number
US07557095B2

Reaction notes

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