Allyl bromide → HCID 15128648, compound

HRID 580417Notes

Reaction equation

HRID 580417 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]([CH:20]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:31](Br)[CH:32]=[CH2:33]>CN(C)C=O>[CH2:33]([C:20]([CH:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])[CH:32]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 15271098HCID 15271098, compound

Product 1

HCID 15128648HCID 15128648, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of [2-(2-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (10 g, 25.81 mmol; see Example 15A) in 51 ml of dry dimethylformamide (0° C., argon) was treated with sodium hydride (6.19 g, 154.86 mmol of a 60% mineral oil dispersion); stirring at 0° C. was continued for 20 minutes. Allyl bromide* (11.17 ml, 129.05 mmol) was added and the reaction was carried out at room temperature for 1 hour, 10 minutes. The reaction was quenched by the slow addition of 1M hydrochloric acid (0° C. ice bath) followed by ethyl acetate. The aqueous layer was washed with ethyl acetate, the combined ethyl acetate layers were washed with 1M hydrochloric acid (3 times), saturated aqueous potassium carbonate solution (2 times), brine, dried over magnesium sulfate and evaporated in vacuo. The crude product was dissolved in dichloromethane and adsorbed onto Celite and filtered through a pad of silica gel (240-400 mesh, hexane, followed by 75/25 hexane/ethyl acetate). Evaporation in vacuo yielded 10.66 g of a viscous yellow-orange oil.

Workup

  1. waitthe reaction was carried out at room temperature for 1 hour, 10 minutes
  2. customThe reaction was quenched by the slow addition of 1M hydrochloric acid (0° C. ice bath)
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe combined ethyl acetate layers were washed with 1M hydrochloric acid (3 times), saturated aqueous potassium carbonate solution (2 times), brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. dissolutionThe crude product was dissolved in dichloromethane
  8. filtrationfiltered through a pad of silica gel (240-400 mesh, hexane, followed by 75/25 hexane/ethyl acetate)
  9. customEvaporation in vacuo

Sources & evidence

ORD record
ord-07a41bb6af324567bb44ddea7f36a1df
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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