Water → HCID 19027008, compound

HRID 1032927Notes

Reaction equation

HRID 1032927 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH2:9][CH3:10])[CH:3]=1.C([Li])CCC.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].O>C(OCC)C>[CH2:9]([C:4]1[CH:3]=[C:2]([Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:7]=[C:6]([CH3:8])[N:5]=1)[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 22317679HCID 22317679, compound2×HCID 178418339Butyllithium

Product 1

HCID 19027008HCID 19027008, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 19.4 g of 4-bromo-2-ethyl-6-methylpyridine from (a) above in 275 ml of diethyl ether chilled to -70° C. under argon was added dropwise over 1/2 hour 38.8 ml of n-butyllithium while maintaining the reaction temperature below -65° C. Stirring was continued at -70° C. for 1 hour and then 22 ml (26.4 g) of tributyltin chloride in 25 ml of diethyl ether were added over 20 minutes. The mixture was allowed to warm to 20° C. and 200 ml of water was added. The ether layer was separated, dried over magnesium sulfate and concentrated in vacuo (90° C.; 50 mm). Hexane was added and the mixture was filtered and the filtrate was concentrated in vacuo (15 mm) to give the title product as a yellow liquid.

Workup

  1. temperaturewhile maintaining the reaction temperature below -65° C
  2. customThe ether layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo (90° C.; 50 mm)
  5. additionHexane was added
  6. filtrationthe mixture was filtered
  7. concentrationthe filtrate was concentrated in vacuo (15 mm)

Sources & evidence

ORD record
ord-a7ed0d4db32a4dc0810d3972586bf1a7
Source dataset
uspto-grants-1994_05
Patent number
US05308843

Reaction notes

Loading…