1,4-Dioxane → HCID 58382000, compound

HRID 1628054Notes

Reaction equation

HRID 1628054 reaction equation
[CH:1](/[C:9]1[N:10]=[C:11]2[CH:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([OH:23])=[O:22])[N:15]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:12]2=[N:13][CH:14]=1)=C\C1C=CC=CC=1.[O:35]1CCOCC1>O.O=[Os](=O)(=O)=O>[CH:1]([C:9]1[N:10]=[C:11]2[CH:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([OH:23])=[O:22])[N:15]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[C:12]2=[N:13][CH:14]=1)=[O:35]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 58382477HCID 58382477, compound

Product 1

HCID 58382000HCID 58382000, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

(E)-3-(2-Styryl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)benzoic acid (0.940 g, 1.99 mmol; prepared using D from Preparation #V.1 with (E)-styrylboronic acid), OsO4 (2.5 wt % in t-BuOH, 1.00 mL, 0.080 mmol) and NaIO4 (1.71 g, 7.97 mmol) were added to a stirred mixture of 1,4-dioxane (10 mL) and water (2 mL) at rt. After about 4.5 h the mixture was diluted with water (30 mL) and extracted with EtOAc (40 mL). The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to provide 3-(2-formyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)benzoic acid (0.792 g, 100%): LC/MS (Table 2, Method c) Rt=1.45 min; MS m/z 398 (M+H)+.

Workup

  1. extractionextracted with EtOAc (40 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5a3c87269fd476a90dd3fe6e9bb27b2
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

Loading…