Ethyl Acetate → HCID 22062410, compound

HRID 251731

Reaction equation

HRID 251731 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+].CCOC(C)=O>CC(C)=O>[N:15]([CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4])=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 691792-Bromo-2'-acetonaphthone

Product 1

HCID 22062410HCID 22062410, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 2-bromo-1-(2-naphthyl)ethanone in acetone was added NaN3 (1 eq.) and the mixture was stirred at RT for 24 h. EtOAc was added (10 vol.) and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica eluting with 10% EtOAc/Petroleum ether to obtain the product as a white solid. 1H NMR (300 MHz, CDCl3) δ: 8.39 (1H, s), 8.02-7.82 (4H, m), 7.69-7.50 (2H, m), 4.68 (2H, s). MS (ES) C12H9N3O requires: 211, found: 212 (M+H)+.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica eluting with 10% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-d7ccc8a8dc384a5893b3d6b1cf413a82
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Linked notes

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