5-Fluoro-2-nitrophenol → (2S)-2-[(5-Fluoro-2-nitrophenoxy)methyl]oxirane

HRID 132581

반응식

HRID 132581 반응식
[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([N+:33]([O-:35])=[O:34])=[C:30](O)[CH:31]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[F:25][C:26]1[CH:31]=[CH:30][C:29]([N+:33]([O-:35])=[O:34])=[C:28]([CH:27]=1)[O:5][CH2:4][C@@H:2]1[CH2:1][O:3]1

참가 물질

6

반응물 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 5460455(+)-GlycidolHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 28109166(2S)-2-[(5-Fluoro-2-nitrophenoxy)methyl]oxirane수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a flask was added (R)-glycidol (0.994 g, 13.4 mmole) and triphenylphosphine (3.52 g, 13.4 mmole) and THF (20 ml, dried over molecular sieves), and 5-fluoro-2-nitrophenol (2.10 g, 13.4 mmole). The mixture was stirred until a homogeneous solution was obtained. The solution was cooled in an ice bath and diethylazodicarboxylate (DEAD, 2.11 ml, 13.4 mmole) was added dropwise over a few minutes. After completed addition, the flask was allowed to reach room temperature and stirred for an additional 2 hours. The solvent was removed in vaccuo and to the residue was added chloroform (5-10 ml). The precipitate (PPh3O) was removed by filtration and the solid was washed with an additional amount of chloroform (5-10 ml). The filtrate was added to a flash column (SiO2, Heptane:Ethyl acetate 4:1), and purified to give 2.02 g (71%) of the sub-title compound as a crystalline material after concentration of pure fractions.

후처리

  1. customwas obtained
  2. temperatureThe solution was cooled in an ice bath
  3. additionaddition
  4. customto reach room temperature
  5. stirringstirred for an additional 2 hours
  6. customThe solvent was removed in vaccuo and to the residue
  7. additionwas added chloroform (5-10 ml)
  8. customThe precipitate (PPh3O) was removed by filtration
  9. washthe solid was washed with an additional amount of chloroform (5-10 ml)
  10. additionThe filtrate was added to a flash column (SiO2, Heptane:Ethyl acetate 4:1)
  11. custompurified

출처 및 근거

ORD 기록
ord-5791f1f45ed74a45a12eb55b525798bc
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388020B2

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