tert-Butyl acetate → HCID 58048570, compound

HRID 1040106Notes

Reaction equation

HRID 1040106 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH3:8].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1(C)C=CC=CC=1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH2:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 10908tert-Butyl acetateHCID 764292-ChlorothiazoleHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 58048570HCID 58048570, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Toluene (60 mL) was placed in a nitrogen-flushed flask and degassed with nitrogen (20 min). 2-chlorothiazole (2.00 g, 16.73 mmol) and tert-butyl acetate (2.137 g, 18.40 mmol) were added, and the mixture was cooled to 0° C. NaHMDS (0.6 M in toluene, 61.3 mL, 36.8 mmol) was added. The reaction was stirred for 2 h at 0° C., allowed to warm to room temperature, and stirred for 18 h. The orange reaction was quenched (under nitrogen) with aqueous saturated NH4Cl. The mixture was extracted with ethyl acetate (2×), and the combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Column chromatography on silica (0-25% ethyl acetate in hexanes) afforded tert-butyl (1,3-thiazol-2-yl)acetate (770 mg, 23%) as a pale yellow oil. MS ESI: [M t-Bu]+ m/z 144.0.

Workup

  1. customflushed flask
  2. customdegassed with nitrogen (20 min)
  3. temperatureto warm to room temperature
  4. stirringstirred for 18 h
  5. customThe orange reaction
  6. customwas quenched (under nitrogen) with aqueous saturated NH4Cl
  7. extractionThe mixture was extracted with ethyl acetate (2×)
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-ac4df315436b45279b856a6be896d719
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

Loading…