Iodine → HCID 10877236, compound

HRID 1008760Notes

Reaction equation

HRID 1008760 reaction equation
[C:1]1([CH2:7][C:8]#[C:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II>C(Cl)Cl.O=[Mn]=O>[C:1]1([CH2:7][C:8]#[C:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 807IodineHCID 12474205HCID 12474205, compound

Product 1

HCID 10877236HCID 10877236, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

4-Phenyl-2-butyn-1-ol (550 mg; 3.76 mmol, obtained as described in Bull. Soc. Chim. Fr, 1954, 816) was dissolved in DCM (10 mL) and MnO2 (1.64 g; 18.8 mmol) was added. The mixture was stirred at rt and the reaction was monitored by TLC (EtOAc/c-Hex 10/90, staining with iodine). MnO2 was regularly added (1.64 g; 18.8 mmol; three times). MnO2 was removed by filtration on a bed of celite. After washing the celite with DCM, the filtrates were then concentrated under reduced pressure. Purification of the crude by flash chromatography on silica (gradient EtOAc/c-Hex 5:95 to 30:70) gave the title compound as an range oil (60 mg, 11% yield). 1H NMR (CDCl3) δ: 9.22 (s, 1H), 7.26 (m, 5H), 3.80 (s, 2H).

Workup

  1. customMnO2 was removed by filtration on a bed of celite
  2. washAfter washing the celite with DCM
  3. concentrationthe filtrates were then concentrated under reduced pressure
  4. customPurification of the crude by flash chromatography on silica (gradient EtOAc/c-Hex 5:95 to 30:70)

Sources & evidence

ORD record
ord-3a6e635dbad84a72bf98816adb22c0d6
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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