Sodium Azide → 2-azido-4-fluoro-2,3-dihydro-1H-inden-1-one

HRID 646718노트

반응식

HRID 646718 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[N-:12]=[N+:13]=[N-:14].[Na+]>CC#N>[N:12]([CH:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])[C:6]1=[O:11])=[N+:13]=[N-:14]

참가 물질

4

반응물 2

HCID 33557Sodium Azide2회HCID 121749864-Fluoro-1-indanone

생성물 1

HCID 866078392-azido-4-fluoro-2,3-dihydro-1H-inden-1-one수율 96%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 4-fluoro-2,3-dihydro-1H-inden-1-one (1.29 g, 9.34 mmol) and HNIB (5.02 g, 12.1 mmol) in CH3CN (190.0 mL) was refluxed for 1.5 h, until the solution was clear yellow. Upon cooling to r.t., NaN3 (1.21 g, 18.7 mmol) was added and the solution was stirred at r.t. for 12 h. Additional NaN3 (0.50 g, 7.7 mmol) was added and the solution stirred further at r.t. for 4 h. The reaction mixture was concentrated in vacuo, and the residue was taken up in CH2Cl2 (100 mL). This solution was washed with H2O (75 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified via column chromatography (SiO2, 5:1 hexanes/EtOAc) to give 1.61 g (96% yield) of 2-azido-4-fluoro-2,3-dihydro-1H-inden-1-one: 1H NMR (400 MHz, CDCl3): 7.59 (d, 1H), 7.41 (m, 1H), 7.32 (t, 1H), 4.15 (dd, 1H), 3.55 (dd, 1H), 2.89 (dd, 1H).

후처리

  1. stirringthe solution stirred further at r.t. for 4 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washThis solution was washed with H2O (75 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via column chromatography (SiO2, 5:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-6a63e3e72a3e44ae9245d8ed18aa04b4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

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