Allyl bromide → HCID 18948412, compound

HRID 1768588Notes

Reaction equation

HRID 1768588 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])CCC.[C:13]1([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(Br)C=C>CCCCCC.O1CCCC1.O>[C:13]1([CH2:23][CH:24]([CH2:7][CH:5]=[CH2:6])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 18948446HCID 18948446, compoundHCID 178418339Butyllithium

Product 1

HCID 18948412HCID 18948412, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 100 ml of anhydrous tetrahydrofuran and 10 ml of diisopropylamine was cooled to -78° C. 51 ml (71.4 mmole) of butyllithium in hexane were added to the mixture, which was then stirred for 15 minutes. At the end of this time, a solution of 12.18 g (47.5 mmole) of t-butyl 3-(1-naphthyl)propionate (prepared as described in Preparation 9) dissolved in 20 ml of anhydrous tetrahydrofuran was added to the reaction mixture, and then the mixture was stirred for 15 minutes. 6.9 g (57 mmole) of allyl bromide were added, and the temperature of the mixture was allowed to rise to room temperature, at which temperature it was stirred for 2 hours. The reaction mixture was then mixed with water and extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of citric acid, with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: a 10: 90 by volume mixture of ethyl acetate and hexane), to afford 12.92 g (91.8%) of the title compound as a pa}e yellow oil.

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe mixture was stirred for 15 minutes
  3. customto rise to room temperature, at which temperature it
  4. stirringwas stirred for 2 hours
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with a saturated aqueous solution of citric acid, with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customThe residue was purified by column chromatography through silica gel (eluent
  11. additiona 10: 90 by volume mixture of ethyl acetate and hexane),

Sources & evidence

ORD record
ord-ffc5e4a2beeb41209f884f5f571ce31f
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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