HCID 68002031, compound → HCID 86660602, compound

HRID 2046025Notes

Reaction equation

HRID 2046025 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([CH:26]([OH:28])C)=[CH:23][C:22]=4[CH:29]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]>O1CCOCC1.O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([CH:26]=[O:28])=[CH:23][C:22]=4[CH:29]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 1

HCID 68002031HCID 68002031, compound

Product 1

HCID 86660602HCID 86660602, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of the product of Step D (0.13 g; 0.34 mmol) and MnO2 (0.15 g; 1.7 mmol) in dioxane (4 ml) was refluxed for 1 h with stirring. After cooling to room temperature, the insoluble material was removed by filtration, washed with EtOAc (20 ml) and combined filtrates were evaporated to dryness to give the title compound (0.13 g; 100%), as greyish solid. 1H-NMR (CDCl3) 9.91 (s, 1H); 8.59 (s, 1H); 8.33 (dd, 1H, J=2, 9 Hz); 7.63-7.82 (m, 4H); 6.99 (d, 1H, J=9 Hz); 4.14-4.26 (m, 4H); 1.4-1.57 (m, 6H+H2O).

Workup

  1. temperaturewas refluxed for 1 h
  2. customthe insoluble material was removed by filtration
  3. washwashed with EtOAc (20 ml)
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-514a75a8a3134120a06ce185769a3477
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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