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

HRID 646718ノート

反応式

HRID 646718 の反応式
[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]

参加物

4

反応物 2

HCID 33557Sodium Azide2 回HCID 121749864-Fluoro-1-indanone

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6a63e3e72a3e44ae9245d8ed18aa04b4
出典データセット
uspto-grants-2010_04
特許番号
US07704995B2

反応ノート

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