Ethylene Glycol → [5-(2-Methyl-[1,3]dioxolan-2-yl)-oxazol-2-yl]-methanol

HRID 2065080Notes

Reaction equation

HRID 2065080 reaction equation
N#N.C([SiH2][O:8][C:9](C)(C)[C:10]1[O:11][C:12]([C:15](=[O:17])[CH3:16])=[CH:13][N:14]=1)(C)(C)C.[CH2:20](O)[CH2:21][OH:22].COC(OC)OC>C([O-])(O)=O.[Na+]>[CH3:16][C:15]1([C:12]2[O:11][C:10]([CH2:9][OH:8])=[N:14][CH:13]=2)[O:17][CH2:20][CH2:21][O:22]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 131730010HCID 131730010, compound

Product 1

HCID 66928789[5-(2-Methyl-[1,3]dioxolan-2-yl)-oxazol-2-yl]-methanol

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-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-5-yl]-ethanone (105 mg, 0.41 mmol) in ethylene glycol (0.46 mL, 8.22 mmol) was treated with trimethylorthoformate (0.09 mL, 0.82 mmol) followed by LiBF4 (8 mg, 0.08 mmol). The reaction mixture was heated at 95° C. until reaction completion. Sat. aq. NaHCO3 (10 mL) was added and the mixture was extracted with EA (2×10 mL). The combined org. extracts were washed with brine (20 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 EA-Hept) gave the title compound as a yellow oil. TLC: rf (4:1 EA-Hept)=0.25. LC-MS-conditions 02: tR=0.56 min; [M+H]+=186.55.

Workup

  1. extractionthe mixture was extracted with EA (2×10 mL)
  2. washextracts were washed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (4:1 EA-Hept)

Sources & evidence

ORD record
ord-6c69a5b57d744e838184d350738f1147
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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