Water → HCID 16110751, compound

HRID 404872Notes

Reaction equation

HRID 404872 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.CCCCCC>[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

7

Reactant 4

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

Product 1

HCID 16110751HCID 16110751, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

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, tributyltin chloride (3.0 mL, 0.011 mol) was added slowly. The solution was then stirred for 3 hours while warming up to room temperature. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed with sat. NH4Cl, brine, and then dried over magnesium sulfate. The solution was filtered, concentrated, and purified to give 4.85 g of the title compound as a clear oil (93% yield). 1H NMR (300 MHz, CDCl3) δ ppm 0.77-1.74 (m, 33H) 4.40-4.63 (m, 1H) 6.84-6.95 (m, 2H) 7.12 (s, 1H) 7.14 (m, 2H). MS (ESI) m/z 526.2 (M+H)+.

Workup

  1. additionwas added slowly
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with sat. NH4Cl, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-130a6eab92e44acc93e23150c47c561d
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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