HCID 57235949, compound → HCID 13343417, compound

HRID 252806Notes

Reaction equation

HRID 252806 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH:15]([C:12]1[CH:13]=[CH:14][C:8]2[O:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:10][C:9]=2[CH:11]=1)=[O:16]

Participants

4

Reactant 1

HCID 57235949HCID 57235949, compound

Product 1

HCID 13343417HCID 13343417, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound 26 (2.53 g, 11.49 mmol) in DCM (70 ml) was added MnO2 (9.99 g, 114.9 mmol). The reaction mixture was stirred at room temperature for 16 h and then filtered through a celite pad. The filtrate was concentrated in vacuum to give the title compound 27 (2.19 g, 87%) as a white solid. 1H-NMR (DMSO) δ: 10.07 (s, 1H), 8.40-8.39 (m, 1H), 8.03 (dd, J=8.6, 1.6 Hz, 1H), 7.93-7.92 (m, 2H), 4.38 (q, J=7.1 Hz, 2H); 1.35 (t, J=7.0, 3H).

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-12d65c3673d640729992bf6d00c163e1
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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