Triacetoxyperiodinane → HCID 86602081, compound

HRID 724686Notes

Reaction equation

HRID 724686 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[S:14](=[O:16])(=[O:15])[N:13]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:12](=[O:24])[CH:11]1[CH3:25].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH:10]1[S:14](=[O:16])(=[O:15])[N:13]([O:17][CH2:18][CH2:19][Si:20]([CH3:22])([CH3:21])[CH3:23])[C:12](=[O:24])[CH:11]1[CH3:25])[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69598033HCID 69598033, compound

Product 1

HCID 86602081HCID 86602081, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-bromo-4-(hydroxymethyl)phenyl]-2-[2-(trimethylsilyl)ethoxy]-methylisothiazolidin-3-one 1,1-dioxide (0.70 g, 1.6 mmol) in methylene chloride (15 mL) was added Dess-Martin periodinane (725 mg, 1.71 mmol) at room temperature. After stirring for 1 h, reaction solution was diluted with diethyl ether, quenched with saturated sodium bicarbonate solution. The aqueous phase was extracted with diethyl ether once. The combined organic solutions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified with silica gel chromatography (5%–50% ethyl acetate/hexanes) to afford product as oil (0.69 g, 99%). 1H NMR (400 MHz, CDCl3): δ 10.01 (s, 1H), 8.21 (d, J=1.6 Hz, 1H), 7.92 (dd, J=8.2, 1.6 Hz, 1H), 7.57 (d, J=8.2 Hz, 1H), 7.38 (m, 4H), 5.60 (dd, J=8.2, 6.2 Hz, 1H), 5.09 (dd, J=15.0, 11.3 Hz, 2H), 3.66 (dd, J=9.2, 7.4 Hz, 2H), 3.56 (dd, J=17.6, 8.2 Hz, 1H), 3.28 (dd, J=17.6, 6.2 Hz, 1H), 0.96 (dd, J=8.6, 7.0 Hz, 2H), 0.01 (s, 9H). LCMS found for C16H23BrNO5SSi (M+H)+: m/z=448, 450.

Workup

  1. customreaction solution
  2. customquenched with saturated sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with diethyl ether once
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel chromatography (5%–50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-72b2f833af2f4840bc152ecbce605151
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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