Perchloric Acid → Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate

HRID 590970노트

반응식

HRID 590970 반응식
Cl(O)(=O)(=O)=O.[OH:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9]>C(OC(C)(C)C)(=O)C>[C:17]([O:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:22])([CH3:18])[CH3:14]

참가 물질

4

반응물 2

HCID 24247Perchloric AcidHCID 70818588Methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate

생성물 1

HCID 70818322Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate수율 83.8%

시약·촉매·용매 1

HCID 10908tert-Butyl acetate용매

실험 절차

Under a nitrogen atmosphere, perchloric acid (70%, 4 mL) was added at −10° C. to a solution of methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate (6a) (800 mg, 3.2 mmol) in terbutyl acetate (25 mL). After 1 hour, the reaction was quenched with a saturated solution of sodium bicarbonate (20 mL) and extracted with dichloromethane (2×20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product (6b) as a white pale oil (410 mg, 1.34 mmol, 42%).

후처리

  1. customthe reaction was quenched with a saturated solution of sodium bicarbonate (20 mL)
  2. extractionextracted with dichloromethane (2×20 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

출처 및 근거

ORD 기록
ord-9fcc35f547584d4ca6793579ec4017a8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

반응 노트

불러오는 중…