Triacetoxyperiodinane → 3-(3,4-Dichlorophenyl)-2-propynal

HRID 639842

Reaction equation

HRID 639842 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH:11]=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 230063813-(3,4-Dichlorophenyl)prop-2-yn-1-ol

Product 1

HCID 592560003-(3,4-Dichlorophenyl)-2-propynalYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3,4-dichlorophenyl)-2-propyn-1-ol (2.980 g, P7, from Method A and B described for P7) in dry DCM (74 mL) and Dess-Martin periodinane (9.43 g) was added. The mixture was stirred at room temperature over night. NaS2O3 (19 g) and NaHCO3 saturated solution were then added to the mixture and it was stirred at room temperature for 1 hour. Then the organic phase was separated and washed with brine. The organic layer was dried and concentrated under reduced pressure to give the crude title product (2.9 g) that was used without further purification.

Workup

  1. stirringwas stirred at room temperature for 1 hour
  2. customThen the organic phase was separated
  3. washwashed with brine
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4086aa00965149cabd01a9265e66cd0d
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Linked notes

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