1-Bromohexane → HCID 18537656, compound

HRID 412379Notes

Reaction equation

HRID 412379 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:35]=[CH:34][C:14]([O:15][C:16]2[CH:17]=[CH:18][C:19]([N+:31]([O-:33])=[O:32])=[C:20]([N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=2)=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:36](Br)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C)C=O>[CH:14]([O:15][CH:16]([CH3:17])[CH3:21])([CH3:34])[CH3:13].[C:3]([O:7][C:8]([N:10]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:11]1[CH:35]=[CH:34][C:14]([O:15][C:16]2[CH:17]=[CH:18][C:19]([N+:31]([O-:33])=[O:32])=[C:20]([N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])[CH:21]=2)=[CH:13][CH:12]=1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 18537685HCID 18537685, compound

Product 2

HCID 7914Diisopropyl EtherHCID 18537656HCID 18537656, compoundYield 192.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (1.26 g 55% w/w) in anhydrous N,N-dimethylformamide (100 ml) was added t-butyl N-[5-(4-t-butoxycarbonylaminophenoxy)-2-nitrophenyl]-N-methylcarbamate (12.1 g). The mixture was stirred at room temperature for several minutes. To this mixture was added hexyl bromide (6.5 g) in an ice bath and the mixture was stirred for 30 minutes and then at room temperature for 1 hour. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using toluene:diisopropyl ether=100:7 as the eluant to afford the desired compound (13.8 g). Rf=0.32: thin layer chromatography on a silica gel plate using toluene/diisopropyl ether=100:7 as the eluant.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-246cd49c7a48480f9ee38cc500864efd
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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