2-Bromopropane → HCID 14651793, compound

HRID 2352203Notes

Reaction equation

HRID 2352203 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:6][O:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[N:3]1.[CH2:19]([Li])[CH2:20][CH2:21]C.BrC(C)C.[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH3:1][C:2]1([CH3:18])[CH2:6][O:5][C:4]([CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:20]([CH3:21])[CH3:19])=[N:3]1

Participants

7

Reactant 4

HCID 63582-BromopropaneHCID 25517Ammonium ChlorideHCID 951032-Oxazoline, 4,4-dimethyl-2-undecyl-HCID 178418339Butyllithium

Product 1

HCID 14651793HCID 14651793, compoundYield 14.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 25.34 g (100 mmoles) of 4,4-dimethyl-2-undecyl-2-oxazoline in 250 ml of dry THF under nitrogen atmosphere was cooled to -78° C. To this was added 62.5 ml (100 mmoles) of 1.6M solution of n-butyl lithium in hexane over a period of 15 minutes and the solution was further stirred for 2 hours. 18.45 g (150 mmoles) of 2-bromopropane was added at -78° C. over a period of 30 minutes and the resulting solution was allowed to warm to room temperature overnight. The solution was poured into 250 ml of saturated ammonium chloride solution and the organic phase was separated. The aqueous phase was extracted with 2×100 ml of ether, the organic phases were combined and extracted with 2×200 ml of brine. After drying over anhydrous magnesium sulphate, the solution was concentrated and the residue was distilled at reduced pressure 10.2 g of starting material was recovered. 8.82 g (50% based on recovered starting material) of product distilled at 131°-134° C./ 0.8 mm Hg. 2.98 g (14.8%) of disubstituted product was obtained as a higher boiling fraction.

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with 2×100 ml of ether
  3. extractionextracted with 2×200 ml of brine
  4. dry with materialAfter drying over anhydrous magnesium sulphate
  5. concentrationthe solution was concentrated
  6. distillationthe residue was distilled at reduced pressure 10.2 g of starting material
  7. customwas recovered
  8. custom8.82 g (50% based on recovered starting material) of product
  9. distillationdistilled at 131°-134° C./ 0.8 mm Hg

Sources & evidence

ORD record
ord-290510345b6c4b04b10fdd4bba8176cd
Source dataset
uspto-grants-1989_10
Patent number
US04876249

Reaction notes

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