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

HRID 1403739Notes

Reaction equation

HRID 1403739 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-4198827657ac4833bfed479794181e5a
Source dataset
uspto-grants-2014_12
Patent number
US08912205B2

Reaction notes

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