Diethyl Ether → HCID 86704448, compound

HRID 1754393Notes

Reaction equation

HRID 1754393 reaction equation
[CH3:1][C:2]1([CH3:7])[N:6]=[CH:5][CH2:4][CH2:3]1.[CH2:8]([Mg]Br)[CH:9]=[CH2:10].C(OCC)C>C1COCC1>[CH2:10]([CH:5]1[NH:6][C:2]([CH3:7])([CH3:1])[CH2:3][CH2:4]1)[CH:9]=[CH2:8]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10942349HCID 10942349, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 86704448HCID 86704448, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5,5-dimethyl-1-pyrroline (2.3 g, 23.7 mmol) in anhydrous THF (50 ml) 1.0 M solution of allylmagnesium bromide in diethyl ether (43.3 ml, 47.3 mmol) was added dropwise at 0° C. The reaction mixture was allowed to stir at 0° C. for 1 hour and brought to room temperature and stirred for 3 hours. Analysis of the reaction mixture by LC-MS indicated the completion of the reaction. The reaction mixture was cooled to 0° C. and quenched with 5 ml of 1N aqueous HCl and partitioned with 50 ml of EtOAc. Organic layer was separated and the aqueous layer was worked up with 2×50 ml of EtOAc. Combined organic layers were dried over MgSO4 and concentrated under vacuum gave the product as light yellow oil in 44% yield (1.5 g). The crude product was taken to the next step without further purification.

Workup

  1. custombrought to room temperature
  2. stirringstirred for 3 hours
  3. customthe completion of the reaction
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customquenched with 5 ml of 1N aqueous HCl
  6. custompartitioned with 50 ml of EtOAc
  7. customOrganic layer was separated
  8. dry with materialCombined organic layers were dried over MgSO4
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1fba204fb6764579a1b5037b483b5aac
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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