Acetic Acid → HCID 66749267, compound

HRID 2174728Notes

Reaction equation

HRID 2174728 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].C([Li])CCC.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](Cl)=[O:23])=[CH:17][CH:16]=1.C(O)(=O)C>O1CCCC1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[O:23][CH:2]=[N:1][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 906924-Chlorophenylacetyl chlorideHCID 533707Ethyl isocyanoacetateHCID 178418339Butyllithium

Product 1

HCID 66749267HCID 66749267, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Ethyl isocyanoacetate (1.00 mL, 9.15 mmol) in Tetrahydrofuran (43 mL) at −78° C. was added 2.5 M n-Butyllithium (9.15 mmol, 9.15 mmol) in hexanes under argon. The mixture was stirred for 20 min. 4-Chlorophenylacetyl chloride (0.753 g, 3.98 mmol) in Tetrahydrofuran (11 mL, 130 mmol) was added at the same temperature. After 1 h, the temperature was raised to rt and then quenched by acetic acid (0.38 g, 6.3 mmol). The mixture was washed with saturated sodium bicarbonate and brine. The organic layer was collected and dried over sodium sulfate. After evaporation, the mixture was purified by chromatography to afford ethyl 5-(4-chlorobenzyl)-1,3-oxazole-4-carboxylate (0.83 g, 78%). LCMS: (FA) ES+ 266.3.

Workup

  1. waitAfter 1 h
  2. washThe mixture was washed with saturated sodium bicarbonate and brine
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. customthe mixture was purified by chromatography

Sources & evidence

ORD record
ord-d7a5fc37fa0e4206808b56929bacaa41
Source dataset
uspto-grants-2015_06
Patent number
US09062038B2

Reaction notes

Loading…