Methyl iodide → Tert-butyl 2-methyl-2-(1,3-thiazol-2-yl)propanoate

HRID 410611

반응식

HRID 410611 반응식
Cl[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:8][CH3:9].[CH3:16][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>C1(C)C=CC=CC=1>[CH3:9][C:8]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([CH3:16])[C:7]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 764292-ChlorothiazoleHCID 88561tert-Butyl propionateHCID 2724254Sodium bis(trimethylsilyl)amide

생성물 1

HCID 67258691Tert-butyl 2-methyl-2-(1,3-thiazol-2-yl)propanoate수율 62%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
0 °C

실험 절차

Toluene (30 mL) was placed in a nitrogen-flushed flask and degassed with nitrogen (20 min). 2-Chlorothiazole (900 mg, 7.53 mmol) and tert-butyl propionate (1.176 g, 9.03 mmol) were added, and the mixture was cooled to 0° C. NaHMDS (0.6 M in toluene, 30.1 mL, 18.06 mmol) was added. The reaction was stirred for 2 h at 0° C., allowed to warm to room temperature, and stirred for 18 h at room temperature. Methyl iodide (3.85 g, 27.1 mmol) was then added. After 1 h at room temperature, 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. Flash chromatography (0-25% ethyl acetate in hexanes) afforded tert-butyl 2-methyl-2-(1,3-thiazol-2-yl)propanoate (1.06 g, 62%) as a pale yellow oil. MS ESI: [M+H]+ m/z 228.1.

후처리

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

출처 및 근거

ORD 기록
ord-bb82558b31444071a7821cc07a9db13c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

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