1-Bromohexane → HCID 68608154, compound

HRID 1991109Notes

Reaction equation

HRID 1991109 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([OH:16])[CH:14]=3)[N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:8]=2)[CH:4]=[N:3]1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CC(C)=O>[CH2:26]([O:16][C:13]1[CH:14]=[C:15]2[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[CH:8][N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:10]2=[N:11][CH:12]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 59128696HCID 59128696, compound

Product 1

HCID 68608154HCID 68608154, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

According to the general procedure using: 27 (60 mg, 0.174 mmol), 1-bromohexane (117 μL, 1.74 mmol), K2CO3 (241 mg, 1.74 mmol) and n-Bu4NI (6.4 mg, 17 μmol) in acetone (4.0 mL) were heated at reflux overnight. Purification by PTLC using AcOEt:hexane=6:4 (v/v) as eluent gave 281 as a clear oil (36 mg, 48%).

Workup

  1. temperatureat reflux overnight
  2. customPurification by PTLC

Sources & evidence

ORD record
ord-2af32ffdb09b4522a137bd0f5913bb8f
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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