Triacetoxyperiodinane → 1-(6-Bromopyridin-2-yl)prop-2-yn-1-one

HRID 386070Notes

Reaction equation

HRID 386070 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:11])[C:9]#[CH:10])[CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[C:9]#[CH:10])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 595262091-(6-Bromopyridin-2-yl)prop-2-yn-1-ol

Product 1

HCID 595263331-(6-Bromopyridin-2-yl)prop-2-yn-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(6-bromopyridin-2-yl)prop-2-yn-1-ol (Example 512 Step 1) (1.00 g, 4.72 mmol) in CH2Cl2 (30 mL) was added Dess-Martin periodinane (4.00 g, 9.43 mmol). The reaction was stirred at room temperature for 2 h. It was subsequently diluted with CH2Cl2 and washed with 20% Na2S2O3. The combined organic layers were dried (MgSO4), filtered, and evaporated. Flash chromatography (0-25% EtOAc/hexanes) afforded the title compound as a colorless solid.

Workup

  1. washwashed with 20% Na2S2O3
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-5b724f1f44b841b78d59da2b477f1d99
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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