Water → HCID 66838443, compound

HRID 2079755Notes

Reaction equation

HRID 2079755 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH3:14])[N:8]=1.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18].O>CCCCC.C(OCC)C>[CH2:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][CH2:17][CH3:18])[N:8]=1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 129548002-Bromo-6-ethylpyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 66838443HCID 66838443, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

Add under nitrogen a solution of tert-butyllithium in pentane (1.5; M, 80.3; mL, 120.5; mmol) dropwise over 1; hour to a cooled solution of 2-bromo-6-ethyl-pyridine (10.19; g, 54.77; mmol) in anhydrous diethyl ether (101.9; mL) at −78° C. at a rate so that the internal reaction temperature does not exceed −75° C. Stir 15; min and add tri-n-butyltin chloride (16.25; mL, 57.51; mmol) dropwise at a rate so that the internal reaction temperature does not exceed −70° C. Warm to room temperature, add water and separate the layers. Extract the aqueous phase once with diethyl ether. Dry the combined organic layers over sodium sulfate, filter and concentrate to give the title compound as a pale yellow liquid (24.05; g, 94%) that is subsequently used without further purification. 1H NMR (CDCl3) δ 0.88; (t, 9H), 1.09; (m, 6H), 1.32; (m, 9H), 1.56; (m, 6H), 1.57; (m, 6H), 2.80; (q, 2H), 6.95; (m, 1H), 7.17; (d, 1H), 7.38; (t, 1H).

Workup

  1. customat −78° C.
  2. customdoes not exceed −75° C
  3. customdoes not exceed −70° C
  4. customseparate the layers
  5. extractionExtract the aqueous phase once with diethyl ether
  6. dry with materialDry the combined organic layers over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-476ce0f639094b799ce3b5a3975491e3
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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