HCID 15665807, compound → HCID 22147870, compound

HRID 630106Notes

Reaction equation

HRID 630106 reaction equation
Cl[C:2]1[S:3][C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[C:5]([Cl:7])[N:6]=1.C([Li])CCC>C1COCC1>[Cl:7][C:5]1[N:6]=[CH:2][S:3][C:4]=1[CH:8]1[O:12][CH2:11][CH2:10][O:9]1

Participants

4

Reactant 2

HCID 15665807HCID 15665807, compoundHCID 178418339Butyllithium

Product 1

HCID 22147870HCID 22147870, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of 2,4-dichloro-5-(1,3-dioxolan-2-yl)-1,3-thiazole (2.9 g, 12.7 mmol) in anhydrous THF (60 mL) was added a solution of butyl lithium (2.5 M in hexanes, 8 mL, 20 mmol). The reaction mixture was stirred at −78° C. for 1.5 hours. The reaction mixture was then quenched with brine (50 mL). The mixture was extracted with EtOAc (3×50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 4-chloro-5-(1,3-dioxolan-2-yl)-1,3-thiazole (2.1 g, 87% yield). The product was used without further purification.

Workup

  1. customThe reaction mixture was then quenched with brine (50 mL)
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fd46ace587b74c5185c8aaa2645dfa1d
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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