2-Butene, 1-bromo-3-methyl- → HCID 20474264, compound

HRID 894411Notes

Reaction equation

HRID 894411 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][CH2:5][N:6]=1.[CH2:7](Br)[CH:8]=[C:9]([CH3:11])[CH3:10].[CH3:13][CH2:14][O-:15].[Na+]>CCCCCC.C(O)C>[CH2:14]([O:15][C:2]1([CH3:1])[N:6]([CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:5][CH2:4][O:3]1)[CH3:13]

Participants

6

Reactant 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 707132-Methyl-2-oxazolineHCID 2723922Sodium ethoxide

Product 1

HCID 20474264HCID 20474264, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
40 °C

Procedure

8.5 g (0.1 mol) of 2-methyloxazoline and 14.9 g (0.1 mol) of prenyl bromide were stirred in 50 ml of n-hexane at 40° C. for 1 hour, whereupon a suspension formed, which, after adding 0.11 mol of a sodium ethylate solution in ethanol, was again stirred at 40° C. for 1 hour. The solution was filtered, the filtrate was concentrated on a rotary evaporator and the residue was distilled using an oil pump. 12.3 g (0.062 mol, 62%) of 2-ethoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidine were isolated at a boiling point 67° C./0.1 mm Hg.

Workup

  1. customformed
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-e6106002d4354b02a66b8de53294ec88
Source dataset
uspto-grants-1981_08
Patent number
US04283544

Reaction notes

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