Sodium hydride → HCID 21492257, compound

HRID 1973558Notes

Reaction equation

HRID 1973558 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH:18]1([CH2:21]Br)[CH2:20][CH2:19]1>CN(C)C=O.C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:21][CH:18]2[CH2:20][CH2:19]2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 79517Ethyl 4-nitrophenylacetateHCID 81503Bromomethylcyclopropane

Product 1

HCID 21492257HCID 21492257, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 21735183Dimethylformamide tolueneSolvent

Procedure

To the solution of 10 g ethyl 4-nitrophenylacetate in 400 ml dimethylformamide-toluene (1:1), 2.5 g 50 percent sodium hydride are added portionwise during 15 minutes while stirring and cooling with ice, after which the solution of 9.6 g cyclopropylmethyl bromide in 50 ml toluene is added dropwise and the mixture stirred overnight at room temperature. It is diluted with 200 ml water, extracted with diethyl ether, the extract dried, evaporated, the residue distilled and the fraction boiling at 132°-138°/0.25 mm Hg collected, to yield the ethyl α-(4-nitrophenyl)-β-cyclopropylpropionate.

Workup

  1. temperaturecooling with ice
  2. stirringthe mixture stirred overnight at room temperature
  3. extractionextracted with diethyl ether
  4. customthe extract dried
  5. customevaporated
  6. distillationthe residue distilled
  7. customthe fraction boiling at 132°-138°/0.25 mm Hg collected

Sources & evidence

ORD record
ord-2b3349fc2f8e48eb85698eeb8bb3f8f9
Source dataset
uspto-grants-1976_12
Patent number
US03997669

Reaction notes

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