Tetrahydrofuran → HCID 18675868, compound

HRID 1635092Notes

Reaction equation

HRID 1635092 reaction equation
[CH:1]1(Br)C[CH2:2]1.[Mg].[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13]Br)[C:8]=1[O:15][CH3:16].[CH2:17]1COCC1>>[Cl:6][C:7]1[C:12]([CH3:17])=[CH:11][N:10]=[C:9]([CH:13]2[CH2:2][CH2:1]2)[C:8]=1[O:15][CH3:16]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 78037BromocyclopropaneHCID 5462224MagnesiumHCID 18675872HCID 18675872, compound

Product 1

HCID 18675868HCID 18675868, compound

Conditions

Temperature
-45 °C

Procedure

Cyclopropyl bromide (0.5 ml) is dissolved in 5 mnl of THF and magnesium (0.15 g) is added and heat is applied to initiate the reaction. Once the reaction is completed, the solution is cooled to −45° C. and cuprous iodide (0.5 g) is added. The reaction is allowed to stir for 30 minutes and 4-Chloro-3-methoxy-2-bromomethyl-pyridine (0.154 g) is added. The reaction is stirred at −45° C. for one hour and allowed to warm at room temperature before being quenched by 5 ml of 28% ammonium hydroxide. The reaction is extracted with ether and the desired product purified by chromatography using hexane/ethyl acetate 9/1 as solvent.

Workup

  1. additionis added
  2. temperatureheat
  3. customthe reaction
  4. stirringThe reaction is stirred at −45° C. for one hour
  5. temperatureto warm at room temperature
  6. custombefore being quenched by 5 ml of 28% ammonium hydroxide
  7. extractionThe reaction is extracted with ether
  8. customthe desired product purified by chromatography

Sources & evidence

ORD record
ord-615e67ab95604eecb7eca7fe4ac70e56
Source dataset
uspto-grants-2003_01
Patent number
US06509349B1

Reaction notes

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