Triacetoxyperiodinane → (2-Phenylthiazol-5-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 70018Notes

Reaction equation

HRID 70018 reaction equation
[C:1]1([C:7]2[S:8][C:9]([CH:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[OH:13])=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([C:7]2[S:8][C:9]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[O:13])=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 53364129(2-Phenylthiazol-5-yl)(3,4,5-trimethoxyphenyl)methanol

Product 1

HCID 53364126(2-Phenylthiazol-5-yl)(3,4,5-trimethoxyphenyl)methanoneYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 40e (0.357 g, 1 mmoL) in 40 mL anhydrous CH2Cl2 was added Dess-Martin reagent (0.848 g, 2 mmol). The mixture was allowed to stir for 30 min and quenched with sat. Na2S2O3 solution, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to give pure compound 1e (80.1%). 1H NMR (CDCl3) δ 8.33 (s, 1H), 8.04 (m, 2H), 7.51 (m, 3H), 7.18 (s, 2H), 3.96 (s, 3H), 3.93 (s, 6H); MS (ESI) m/z 378.1 (M+H)+.

Workup

  1. customquenched with sat. Na2S2O3 solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-fbdad3f75e1842a6950c0efc79d1ea6f
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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