Ethylene Glycol → HCID 7099161, compound

HRID 2064972Notes

Reaction equation

HRID 2064972 reaction equation
N#N.[Br:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[N:8][CH:9]=1.[CH2:13](O)[CH2:14][OH:15].COC(OC)OC.C([O-])([O-])=O.[Na+].[Na+]>>[Br:3][C:4]1[CH:9]=[N:8][CH:7]=[C:6]([C:10]2([CH3:11])[O:15][CH2:14][CH2:13][O:12]2)[CH:5]=1

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 8204233-Acetyl-5-bromopyridine

Product 1

HCID 7099161HCID 7099161, compound

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(5-bromo-pyridin-3-yl)-ethanone (1800 mg, 9.00 mmol) in ethylene glycol (9.57 mL, 171.69 mmol) was treated with trimethylorthoformate (2.01 mL, 18.34 mmol) followed by LiBF4 (172 mg, 1.80 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. Na2CO3 was added and the mixture was extracted twice with ether. The combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (50:50 hept-EA)=0.57. LC-MS-conditions 02: tR=0.87 min.

Workup

  1. extractionthe mixture was extracted twice with ether
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (20:1 hept-EA)

Sources & evidence

ORD record
ord-3addac9df0074140ae656703f7122279
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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