Water → 4-Isopropyl-2-(tributylstannyl)thiazole

HRID 925946Notes

Reaction equation

HRID 925946 reaction equation
[CH:1]([C:4]1[N:5]=[CH:6][S:7][CH:8]=1)([CH3:3])[CH3:2].[Li]CCCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].O>C1COCC1>[CH:1]([C:4]1[N:5]=[C:6]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 200843694-IsopropylthiazoleHCID 178418339Butyllithium

Product 1

HCID 575787544-Isopropyl-2-(tributylstannyl)thiazoleYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-isopropylthiazole (9 g, 71 mmol) in anhydrous THF (100 mL) at −78° C. was added nBuLi (40 mL, 99 mmol). The reaction was stirred for 1 hr and the temperature reached −40° C. The reaction mixture was cooled to −78° C. and tri-n-butyltinchloride (23 g, 71 mmol) was added. The reaction mixture was stirred at room temperature for 48 hrs. Water was added and solvent was evaporated under reduced pressure. The residue was partioned between water and EtOAc. Organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 219 as colorless oil in 55% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 0.88-1.62 (m, 27H), 1.40 (s, 3H), 1.42 (s, 3H), 3.17-3.24 (m, 1H).

Workup

  1. customreached −40° C
  2. stirringThe reaction mixture was stirred at room temperature for 48 hrs
  3. customsolvent was evaporated under reduced pressure
  4. dry with materialOrganics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-031d12fa24294639b839f8f1e5449b36
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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