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

HRID 5980
Notes
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Reaction equation

HRID 5980 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

(+-)-(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.

Workup

  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)

Sources & evidence

ORD record
ord-461d76bc7b794e33b5c526fa6f430a5a
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05246956

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes