Triacetoxyperiodinane → 4-Hydroxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-one

HRID 1776282Notes

Reaction equation

HRID 1776282 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:16])[C:10]#[C:11][C:12]([CH3:15])([OH:14])[CH3:13])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[OH:14][C:12]([CH3:15])([CH3:13])[C:11]#[C:10][C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[O:16]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59354753HCID 59354753, compound

Product 1

HCID 127225774-Hydroxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature, stirred solution of 1-(4-methoxyphenyl)-4-methylpent-2-yne-1,4-diol (6.3 g, 0.029 mol) in DCM (50 mL), Dess Martin periodinane (31.2 g, 0.07 mol) was added and the reaction mixture was stirred for 3 h. The reaction mixture was then diluted with DCM (50 mL) and the combined organic layers were washed with a saturated NaHCO3 solution and water, dried over Na2SO4, filtered and then concentrated in vacuo to afford 4-hydroxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-one (6 g, 96%) as an oil.

Workup

  1. additionwas added
  2. washthe combined organic layers were washed with a saturated NaHCO3 solution and water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d94357488c04e59b65e22596704d26d
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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