Hexane → 4-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazole

HRID 51102Notes

Reaction equation

HRID 51102 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[N:6]=1.C([Li])CCC.CCCCCC.[CH2:23]([Sn:27](Cl)([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>C1COCC1.O>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[C:5]1[N:6]=[CH:2][S:3][C:4]=1[Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 219522862-Bromo-4-(1,3-dioxolan-2-yl)thiazoleHCID 178418339Butyllithium

Product 1

HCID 219520694-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazoleYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-4-(1,3-dioxolan-2-yl) thiazole (6.4 g, 27.14 mmol) was stirred at −78° C. in dry THF (38 ml). 1.6M n butyl lithium in hexane (18.6 ml, 29.78 mmol) was added dropwise under nitrogen. After 30 min at this temperature, tributyl tin chloride (7.35 ml, 27.14 mmol) was added dropwise. The reaction was allowed to warm to 0° and water (20 ml) was added. The product was extracted into ether (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated. The residue was triturated with isohexane (3×100 ml) and the mother liquors were decanted, combined and concentrated to give a brown oil (11.88 g); m/z 444-450.

Workup

  1. temperatureto warm to 0°
  2. extractionThe product was extracted into ether (3×100 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated with isohexane (3×100 ml)
  6. customthe mother liquors were decanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-71867021d5ac45dcb699b47f55b14fd4
Source dataset
uspto-grants-2004_03
Patent number
US06713485B2

Reaction notes

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