Pentane → ethyl 5-[(E)-(2-imidazol-1-yl-3,4-dihydro-2H-naphthalen-1-ylidene)amino]oxypentanoate

HRID 5980

反応式

HRID 5980 の反応式
[N:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)/[C:7]/2=[N:16]\[OH:17])[CH:5]=[CH:4][N:3]=[CH:2]1.CCCCC.[H-].[Na+].[CH2:25]([O:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]Br)[CH3:26]>CN(C=O)C>[CH2:25]([O:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][O:17]/[N:16]=[C:7]1/[CH:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:15][CH2:14][C:13]2[C:8]/1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:26]

参加物

6

反応物 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 88465041(NE)-N-(2-imidazol-1-yl-3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine

生成物 1

HCID 19794644ethyl 5-[(E)-(2-imidazol-1-yl-3,4-dihydro-2H-naphthalen-1-ylidene)amino]oxypentanoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

(+-)-(E)-2-(1H-imidazol-1-yl)-1,2,3,4-tetrahydronaphtalen-1-one oxime (500 mg; 2.2 mmoles) dissolved in dry DMF (27 ml) is added, under dry nitrogen atmosphere, to a pentane-washed sodium hydride suspension (160 mg NaH 55%; 3.6 mmoles), in dry DMF (10 ml). The resulting reaction mixture is stirred at r.t. for 2 hours. Then ethyl-5-bromopentanoate (0.530 ml; 3.3 mmoles) is added at r.t. and the reaction mixture is stirred at r.t. for 3 hrs., the solvent evaporated in vacuo, and the residue carefully taken up with ice-cooled water and extracted with ethyl acetate. The collected organic phases are dried over Na2SO4 and evaporated to give an oily crude material which is chromatographed over silica gel. By eluting with CH2Cl2 /MeOH (95:5), the pure title compound is obtained as a slight yellow oil (250 mg). 1H-NMR (200MH2, CDCl3) ppm.

後処理

  1. customThe resulting reaction mixture
  2. stirringthe reaction mixture is stirred at r.t. for 3 hrs
  3. custom, the solvent evaporated in vacuo
  4. temperaturecooled water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe collected organic phases are dried over Na2SO4
  7. customevaporated
  8. customto give an oily crude material which
  9. customis chromatographed over silica gel
  10. washBy eluting with CH2Cl2 /MeOH (95:5)

出典と根拠

ORDレコード
ord-461d76bc7b794e33b5c526fa6f430a5a
出典データセット
uspto-grants-1993_09
特許番号
US05246956

関連ノート

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