HCID 66615038, compound → HCID 86660602, compound

HRID 717609Notes

Reaction equation

HRID 717609 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]([CH2:26][OH:27])=[CH:23][C:22]=4[CH:28]=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:27])=[CH:23][C:22]=4[CH:28]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 1

HCID 66615038HCID 66615038, 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-43ca230cc4cc426c9a9d12165c368498
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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