Sulfuric Acid → HCID 58522244, compound

HRID 1898542Notes

Reaction equation

HRID 1898542 reaction equation
[OH:1][S:2]([OH:5])(=[O:4])=[O:3].[O:6]([C:13]1[N:14]=[C:15]2[C:21]([CH:22]=[O:23])=[CH:20][N:19]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)=[O:34].OS(O)(=O)=O.[O:41]=[Cr:42](=[O:44])=[O:43]>O.CC(C)=O>[CH3:8][C:7]([CH3:12])=[O:6].[OH:4][S:2]([OH:5])(=[O:3])=[O:1].[O:41]=[Cr:42](=[O:44])=[O:43].[O:6]([C:13]1[N:14]=[C:15]2[C:21]([C:22]([OH:34])=[O:23])=[CH:20][N:19]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 86657872HCID 86657872, compoundHCID 131709961Jones' reagent

Product 2

HCID 58522244HCID 58522244, compoundYield 65%HCID 131709961Jones' reagent

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stock solution of Jones reagent (2.67 M) was prepared by carefully adding concentrated H2SO4 (2.3 mL) to CrO3 (2.67 g) then diluting to 10 mL with H2O. To a solution of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (2.35 g, 6.37 mmol) in acetone (75 mL) at 0° C. was added Jones reagent (5 mL, 13.4 mmol) dropwise. The reaction mixture was stirred at room temperature for 2 h then quenched with i-PrOH (2 mL), diluted with EtOAc, and filtered over Celite, rinsing with EtOAc. The filtrate was washed with cold water (3×) and brine then dried over MgSO4 and concentrated. The residue was purified by SiO2 column chromatography (30-70% EtOAc/hexanes) to provide 1.59 g (65%) of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a light yellow solid.

Workup

  1. customthen quenched with i-PrOH (2 mL)
  2. additiondiluted with EtOAc
  3. filtrationfiltered over Celite
  4. washrinsing with EtOAc
  5. washThe filtrate was washed with cold water (3×) and brine
  6. dry with materialthen dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 column chromatography (30-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2587571e667f49f8893a9ba405689aea
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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