Ethylene Glycol → HCID 131730003, compound

HRID 2065029Notes

Reaction equation

HRID 2065029 reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:20])([CH3:19])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16](=[O:18])[CH3:17])[CH:11]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:21](O)[CH2:22][OH:23].COC(OC)OC>C([O-])(O)=O.[Na+]>[C:3]([SiH2:7][O:8][C:9]([CH3:20])([CH3:19])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2([CH3:17])[O:23][CH2:22][CH2:21][O:18]2)[CH:11]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 131729997HCID 131729997, compound

Product 1

HCID 131730003HCID 131730003, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a condenser under inert atmosphere (N2), a solution of 1-[4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethanone (1.78 g, 6.71 mmol) in ethylene glycol (7.14 mL, 127.95 mmol) was treated with trimethylorthoformate (1.50 mL, 13.67 mmol) followed by LiBF4 (128 mg, 1.34 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. NaHCO3 (50 mL) was added and the mixture was extracted with EA (50 mL). The org. extracts were washed with brine (2×50 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 1:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (1:1 hept-EA)=0.50. LC-MS-conditions 02: tR=0.91 min, [M+H]+=310.40.

Workup

  1. extractionthe mixture was extracted with EA (50 mL)
  2. washextracts were washed with brine (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (20:1 to 1:1 hept-EA)

Sources & evidence

ORD record
ord-4105e1f8c5b34a58a4781971126b105e
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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