Water → 1-Allyl 7-ethyl 2-allyloxycarbonyl-2-[2-(4-cyanophenyl)ethyl]heptandioate

HRID 1672672Notes

Reaction equation

HRID 1672672 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]([CH:9]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])=[O:8])[CH:4]=[CH2:5].Br[CH2:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=1.O>CN(C=O)C>[CH2:3]([O:6][C:7]([C:9]([CH2:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=1)([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])=[O:8])[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 128865484-(2-Bromoethyl)benzonitrileHCID 578313641-Allyl 7-ethyl 2-allyloxycarbonylheptanedioate

Product 1

HCID 578313401-Allyl 7-ethyl 2-allyloxycarbonyl-2-[2-(4-cyanophenyl)ethyl]heptandioateYield 27,923.199%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

6.37 g (159.27 mmol; content 60%) of sodium hydride are added in portions to a solution of 45.23 g (144.79 mmol) of 1-allyl 7-ethyl 2-allyloxycarbonylheptanedioate from Example 82A in 250 ml of DMF at 0° C. The reaction solution is then allowed to reach room temperature and is stirred for 30 min. The reaction solution is then cooled to 0° C. and, after addition of 36.50 g (173.75 mmol) of 4-(2-bromoethyl)benzonitrile from Example 8A in 250 ml DMF, stirred at this temperature for 30 min. The mixture is then stirred at room temperature overnight. Water is added dropwise to the reaction mixture and, after extraction three times with ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is concentrated to dryness in vacuo. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1-4:1→1:1). 17.85 g (40.43 mol, 28% yield) of a colorless solid are obtained.

Workup

  1. customto reach room temperature
  2. stirringstirred at this temperature for 30 min
  3. stirringThe mixture is then stirred at room temperature overnight
  4. extractionafter extraction three times with ethyl acetate
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe solvent is concentrated to dryness in vacuo
  9. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1-4:1→1:1)

Sources & evidence

ORD record
ord-a016309c809a41899a2848808b5c2c17
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

Loading…