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Ethyl Acetate → HCID 45092074, 화합물

HRID 525351
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HRID 525351 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])C)C(O)(C)C.CC(C)([O-])C.[K+].CCOC(C)=O>C1COCC1.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:16]([CH3:18])([CH3:19])[O:15][C:14](=[O:20])[NH:13]1
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참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 89827431HCID 89827431, 화합물

생성물 1

HCID 45092074HCID 45092074, 화합물수율 98.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of tert-butyl (1-(2-fluorophenyl)-2-hydroxy-2-methylpropyl)carbamate (400 mg, 1.41 mmol) in THF (8 mL) was added potassium tert-butoxide (316.87 mg, 2.82 mmol) at 0-5° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was quenched with ice water and extracted with EtOAc. The combined organic layers were washed with, water, saturated NaCl solution and dried on Na2SO4, filtered, and concentrated under reduced pressure to afford 4-(2-fluorophenyl)-5,5-dimethyloxazolidin-2-one (290 mg, 98.18%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.05 (s, 1H), 7.44-7.35 (m, 2H), 7.30-7.22 (m, 2H), 4.88 (s, 1H), 1.53 (s, 3H), 0.88 (s, 3H). m/z (ESI) 210.1 (M+H)+.

후처리

  1. customThe resulting reaction mixture
  2. customthe reaction mixture was quenched with ice water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with, water, saturated NaCl solution
  5. customdried on Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e103b8d826e64ec78f57be63b2010e06
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340549B2

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