Water → 2-(4-Isopropoxy-phenoxy)-5-tributylstannanyl-thiazole

HRID 1028461Notes

Reaction equation

HRID 1028461 reaction equation
[CH:1]([O:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C([Li])CCC.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].O>O1CCCC1>[CH:1]([O:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][C:10]2[S:11][C:12]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 670969222-(4-Isopropoxyphenoxy)-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 161107512-(4-Isopropoxy-phenoxy)-5-tributylstannanyl-thiazoleYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 1B (2.4 g, 0.01 mol) in dry tetrahydrofuran was added n-butyl lithium (4.4 mL, 2.5 M in hexane) at −78° C. drop wise. After stirring at this temperature for 1 h, tributyltin chloride (3.0 mL, 0.011 mol) was added slowly to the mixture. The brown solution was then stirred for 3 hours while warning up to room temperature. Water was added and the solution was extracted with ethyl acetate. The organic layer washed with saturated NH4Cl, brine, and then dried over magnesium sulfate. The solution was concentrated and the crude was purified on a silica gel flash column, eluting with 5-30% EtOAc in hexane, to give 4.85 g of the title compound (93% yield), 1H NMR (300 MHz, CDCl3) δ ppm 0.77-1.74 (m, 33 H) 4.40-4.63 (m, 1 H) 6.84-6.95 (m, 2 H) 7.12 (s, 1 H) 7.14-7.23 (m, 2 H). MS (ESI), m/z 526.2 (M+H)+.

Workup

  1. stirringThe brown solution was then stirred for 3 hours
  2. customwhile warning up to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer washed with saturated NH4Cl, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated
  7. customthe crude was purified on a silica gel flash column
  8. washeluting with 5-30% EtOAc in hexane

Sources & evidence

ORD record
ord-744424346070415cb618dd3508734a82
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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