Water → 2-Methyl-4-(tributylstannyl)-1,3-thiazole

HRID 1445431Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.C([Li])CCC.[CH2:13]([Sn:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].O>C1COCC1>[CH3:7][C:4]1[S:5][CH:6]=[C:2]([Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH3:16])[N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-bromo-2-methylthiazole (950 mg, 5.3 mmol) in absolute THF (40 mL) at −78° C. was added dropwise n-butyllithium (2.7 mL, 1.6 M in hexane). The solution was stirred at −78° C. for 1 h, then tributyltinchloride (2.2 g, 6.8 mmol) was added, and the mixture was allowed to warm to room temperature. Water (90 mL) was poured into the reaction mixture and the phases were separated. The aqueous layer was extracted with diethyl ether (4×30 mL). The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. The resulting oil was purified by fractionated Kugelrohr distillation to give the title compound (2.3 g). The product was used without further purification.

Workup

temperatureto warm to room temperature
customthe phases were separated
extractionThe aqueous layer was extracted with diethyl ether (4×30 mL)
dry with materialThe combined organic phases were dried over magnesium sulfate
customthe solvent was removed in vacuo
distillationThe resulting oil was purified by fractionated Kugelrohr distillation

Sources & evidence

ORD record: ord-cc0b212c75f043d4883485e2da62ad34
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666834B2

Reaction notes

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