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

HRID 63194Notes

Reaction equation

HRID 63194 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[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:8]=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:11][CH:10]=[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:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 53364128(5-Phenylthiophen-3-yl)(3,4,5-trimethoxyphenyl)methanol

Product 1

HCID 53364124(5-Phenylthiophen-3-yl)(3,4,5-trimethoxyphenyl)methanoneYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 40f (0.260 g, 0.73 mmoL) in 20 mL anhydrous CH2Cl2 was added Dess-Martin reagent (0.465 g, 1.36 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 1f as light yellow crystals (60.9%). 1H NMR (CDCl3) δ 7.97 (d, 1H, J=1.5 Hz), 7.82 (d, 1H, J=1.5 Hz), 7.59-7.57 (m, 2H), 7.45-7.34 (m, 3H), 7.19 (s, 2H), 3.95 (s, 3H), 3.93 (s, 6H); MS (ESI) m/z 355.1 (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-c7ebdfddd3ed433fab7b08138b7c69c5
Source dataset
uspto-grants-2016_09
Patent number
US09447049B2

Reaction notes

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