1-Bromopentane → HCID 68607058, compound

HRID 1991108Notes

Reaction equation

HRID 1991108 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][CH3:30].C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CC(C)=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([O:16][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[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

Participants

6

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 59128696HCID 59128696, compound

Product 1

HCID 68607058HCID 68607058, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

According to the general procedure using: 27 (60 mg, 0.174 mmol), 1-bromopentane(129 μL, 1.05 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 28k as a clear oil (38 mg, 51%).

Workup

  1. temperatureat reflux overnight
  2. customPurification by PTLC

Sources & evidence

ORD record
ord-652e3dc17ea94f47bf93074ef1592316
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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