Dimethylformamide → HCID 67262257, compound

HRID 1040107Notes

Reaction equation

HRID 1040107 reaction equation
[H-].[Na+].CN(C=O)C.[S:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Br[CH2:22][CH2:23]Br>C1COCC1>[S:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 58048570HCID 58048570, compound

Product 1

HCID 67262257HCID 67262257, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (702 mg, 17.56 mmol) was suspended in THF (7 mL)/DMF (7 mL) under nitrogen and cooled to 0° C. The product from Step 1 (875 mg, 4.39 mmol) in THF (3 mL)/DMF (3 mL) was added dropwise. The ice bath was removed, and the yellow-orange suspension was stirred at room temperature for 30 min. The mixture was then cooled back down to 0° C., and 1,2-dibromoethane (2.475 g, 13.17 mmol) was added in one portion. The reaction was allowed to warm to room temperature and stirred for 2 h. It was then quenched with saturated NH4Cl and water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (Na2SO4), and evaporated. Flash chromatography (0-20% ethyl acetate in hexanes) afforded tert-butyl 1-(1,3-thiazol-2-yl)cyclopropanecarboxylate (866 mg, 88%) as a colorless oil. MS ESI: [M+H]+ m/z 226.1.

Workup

  1. customThe ice bath was removed
  2. additionwas added in one portion
  3. temperatureto warm to room temperature
  4. stirringstirred for 2 h
  5. customIt was then quenched with saturated NH4Cl and water
  6. extractionextracted with ethyl acetate (2×)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-9ca97b94aca441bfb80adc7fcd6b0c46
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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