Dimethylformamide → HCID 18946532, compound

HRID 1769015Notes

Reaction equation

HRID 1769015 reaction equation
[Cl:1]C1(O)NC=CC=C1.[CH3:9][CH2:10][CH2:11]CCC.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26].[CH3:27][N:28](C)[CH:29]=[O:30]>>[Cl:1][C:27]1[N:28]=[C:29]([O:30][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 8058HexaneHCID 24758Sodium hydrideHCID 1626071-Octanol, 8-bromo-HCID 18946538HCID 18946538, compound

Product 1

HCID 18946532HCID 18946532, compound

Procedure

6-Chloro-6-hydroxypyridine (Aldrich) (1.94 g, 15 mmol) in dry dimethylformamide (DMF) (3 ml) was added to a suspension of hexane washed sodium hydride (18 mmol) in dry DMF (11 ml). After stirring at room temperature for 2 hours, 8-bromo-octan-1-ol (3.15 g) was added. The mixture was warmed at 60° for 2 hours and left at room temperature for 16 hours. After conventional work-up and chromatography on silica, 8-(6'-chloro-2-pyridyl)oxyoctan-1-ol was obtained.

Workup

  1. temperatureThe mixture was warmed at 60° for 2 hours
  2. waitleft at room temperature for 16 hours

Sources & evidence

ORD record
ord-55143c3601d1476ba6f9aa69927992be
Source dataset
uspto-grants-1995_01
Patent number
US05380732

Reaction notes

Loading…