2,6-Lutidine → HCID 66728774, compound

HRID 1098585Notes

Reaction equation

HRID 1098585 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[O:3].N1C(C)=CC=CC=1C.[CH3:17][C:18]([CH3:22])([CH3:21])[C:19]#[N:20]>>[C:18]([C:19]1[O:3][C:2]([C:1]([O:6][CH2:7][CH3:8])=[O:5])=[CH:4][N:20]=1)([CH3:22])([CH3:21])[CH3:17]

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 12041Ethyl pyruvateHCID 12416Pivalonitrile

Product 1

HCID 66728774HCID 66728774, compoundYield 29%

Procedure

A solution of ethyl pyruvate (2.0 g, 17.2 mmol) and HDNIB (9.7 g, 20.7 mmol) in trimethylacetonitrile (15 mL) was heated to reflux for 3 hours. After the reaction mixture was cooled to RT, 2,6-lutidine (0.2 mL, 1.7 mmol) was added. The reaction mixture was refluxed for an additional 8 hours. The reaction was checked by LC-MS and the solvent was removed. The residue was dissolved in CH2Cl2C washed with water and brine, dried (Na2SO4), concentrated in vacuo and purified via silica gel column chromatography (EtOAc/hexane) to obtain ethyl 2-tert-butyloxazole-5-carboxylate (1.0 g, 29% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.89 (s, 1H), 4.42 (d, J=7.2 Hz, 2H), 1.49 (s, 9H), 1.43 (d, J=7.2 Hz, 3H); MS (ESI) m/z: 198.1 (M+H+).

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureThe reaction mixture was refluxed for an additional 8 hours
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved in CH2Cl2C
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. custompurified via silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-6740de7426e64ae0a226b8380a399d4e
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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