Tributyltin Chloride → 4-Isopropyl-2-(tributylstannyl)thiazole

HRID 530758Notes

Reaction equation

HRID 530758 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]([CH3:9])[CH3:8])[N:6]=1.[Li]CCCC.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>CCOCC>[CH:7]([C:5]1[N:6]=[C:2]([Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][CH2:17][CH3:18])[S:3][CH:4]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 98342752-Bromo-4-(propan-2-yl)-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 575787544-Isopropyl-2-(tributylstannyl)thiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 2-bromo-4-isopropyl-thiazole (6.79 mmol) in anhydrous Et2O (30 mL) under nitrogen at −78° C. was added dropwise nBuLi (7.47 mmol). The reaction was stirred for 30 min and the temperature reached to −40° C. The reaction mixture was cooled down to −78° C. and tri-n-butyltinchloride (8.15 mmol) was added slowly. The reaction mixture was allowed to warm up to room temperature and stirred during 36 hrs. Et2O was added and the reaction was quenched with saturated NH4Cl. The organic layer was washed with saturated NH4Cl and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give compound 219 as a pale yellow oil in quantitative yield.

Workup

  1. customreached to −40° C
  2. temperatureto warm up to room temperature
  3. stirringstirred during 36 hrs
  4. customthe reaction was quenched with saturated NH4Cl
  5. washThe organic layer was washed with saturated NH4Cl and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8ee3eac3aea4270aa376a79989cec12
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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