Allyl bromide → HCID 10081135, compound

HRID 2270494Notes

Reaction equation

HRID 2270494 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[Li+].[CH3:13][CH:14]([N-]C(C)C)[CH3:15].C(Br)C=C>C1COCC1>[O:11]=[C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]1[CH2:15][CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 682662-TetraloneHCID 2724682Lithium diisopropylamide

Product 1

HCID 10081135HCID 10081135, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7.3 g (50 mmol) 2-tetralone in 75 mL THF in a 3-neck round-bottomed flask, equipped with a gas inlet and septum, was added 36.7 mL LDA (55 mmol, 1.5 M in cyclohexane) at −30° C. under a nitrogen atmosphere. The solution was allowed to warm to 0° C. over a 30-minute period and 5.6 mL (65 mmol) allyl bromide was added. TLC analysis was used to monitor the reaction. After stirring for 24 hours at room temperature, the reaction mixture was quenched with 10% sodium bisulfate to pH 2-3. After removal of THF under reduced pressure, the mixture was extracted with ethyl acetate (2×1 L) and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by liquid chromatography on 800 g of silica gel 60 (230-400 m), eluting with 1 L of hexane, followed by 5 L of 5% ethyl acetate/hexane, and collecting 40 mL fractions. Fractions 65-82 gave 3.1 g (33%) of pure 1,2,3,4-Tetrahydro-2-oxo-1-(2-propenyl)-naphthalene as a light yellow oil.

Workup

  1. customthe reaction
  2. customthe reaction mixture was quenched with 10% sodium bisulfate to pH 2-3
  3. customAfter removal of THF under reduced pressure
  4. extractionthe mixture was extracted with ethyl acetate (2×1 L)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by liquid chromatography on 800 g of silica gel 60 (230-400 m)
  10. washeluting with 1 L of hexane
  11. customcollecting 40 mL fractions

Sources & evidence

ORD record
ord-815fad15709e4c51ab26388c16545e02
Source dataset
uspto-grants-2001_12
Patent number
US06331636B1

Reaction notes

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