27913-19-5 → HCID 59776371, compound

HRID 1008763Notes

Reaction equation

HRID 1008763 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH:11]=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 1518463427913-19-5

Product 1

HCID 59776371HCID 59776371, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-methoxyphenyl)prop-2-yn-1-ol (500 mg, 3.08 mmol) in anhydrous DCM (20 ml) under argon was added MnO2 (7.8 g, 90 mmol) portion wise over 2 h. The reaction mixture was stirred at rt for one additional hour. Then the reaction mixture was filtered and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel (cHex:EtOAc, gradient 9:1 to 4:1) gave 122 mg (25%) of the title compound as a yellow oil. HPLC, Rt: 2.9 min (purity: 99.9%). 1H NMR (CDCl3) δ: 9.43 (s, 1H), 7.32 (dd, J=8.3, 7.7 Hz, 1H), 7.22 (ddd, J=7.7, 1.4, 1.1 Hz, 1H), 7.12 (dd, J=2.6, 1.4 Hz, 1H), 7.05 (ddd, J=8.3, 2.6, 1.1 Hz, 1H), 3.83 (s, 3H).

Workup

  1. filtrationThen the reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customPurification by flash chromatography on silica gel (cHex:EtOAc, gradient 9:1 to 4:1)

Sources & evidence

ORD record
ord-71594e790d2b4f798690cd1ff437b633
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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