Pyridine → Undec-10-en-1-yl 2-bromo-2-methylpropanoate

HRID 1170034Notes

Reaction equation

HRID 1170034 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].N1C=CC=CC=1.[Br:19][C:20]([CH3:25])([CH3:24])[C:21](Br)=[O:22]>O1CCCC1.CCCCCC>[Br:19][C:20]([CH3:25])([CH3:24])[C:21]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])=[O:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 818510-Undecen-1-olHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 23113089Undec-10-en-1-yl 2-bromo-2-methylpropanoateYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4.257 g (25 mmol) of ω-undecylenyl alcohol in 25 mL of dry tetrahydrofuran was added 2.1 mL of pyridine (26.5 mmol) followed by dropwise addition of 3.10 mL of 2-bromoisobutyryl bromide (25 mmol) over 5 min. The mixture was stirred at room temperature overnight and then diluted with hexane (50 mL) and washed with 2 N HCl and twice with water. The organic phase was dried over sodium sulfate and filtered. The solvent was removed from the filtrate under reduced pressure, and the colorless oily residue was purified by flash column chromatography (hexane/ethyl acetate 25/1 v/v) to give 7.34 g (92%) of the ester as a colorless oil.

Workup

  1. washwashed with 2 N HCl and twice with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed from the filtrate under reduced pressure
  5. customthe colorless oily residue was purified by flash column chromatography (hexane/ethyl acetate 25/1 v/v)

Sources & evidence

ORD record
ord-adf84ce4536a41f690f3cd7fd8825f62
Source dataset
uspto-grants-2010_11
Patent number
US07825199B1

Reaction notes

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