Hydrochloric Acid → HCID 68227210, compound

HRID 1400135Notes

Reaction equation

HRID 1400135 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+].Br[CH2:19][CH2:20][CH2:21]Br.Cl>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:21][CH2:20][CH2:19]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 68227210HCID 68227210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

10 g of ethyl 4-nitrophenylacetate are dissolved in 100 ml of DMF, added dropwise to a suspension of 4.97 g of sodium hydride in 20 ml of DMF with ice-cooling and stirred for 30 min. 6.6 ml of 1,3-dibromopropane are subsequently added, and the mixture is stirred at 23° C. for 12 h. The reaction mixture is subsequently stirred into a mixture of 100 ml of 1 N hydrochloric acid and 200 g of ice. The mixture is washed four times with 100 ml of ethyl acetate each time, the combined organic phases once with 100 ml of sodium chloride solution, dried over sodium sulfate and, after filtration, evaporated to dryness in vacuo. The residue is purified by column chromatography (reversed phase). Yield: 5.5 g (46%) of ethyl 1-(4-nitrophenyl)cyclobutanecarboxylate; LC-MS retention time: 2.21 min (“nonpolar” gradient);

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at 23° C. for 12 h
  3. washThe mixture is washed four times with 100 ml of ethyl acetate each time
  4. dry with materialthe combined organic phases once with 100 ml of sodium chloride solution, dried over sodium sulfate
  5. filtrationafter filtration
  6. customevaporated to dryness in vacuo
  7. customThe residue is purified by column chromatography (reversed phase)

Sources & evidence

ORD record
ord-bf7f9a49c0324c7ea2deeb625157ab1a
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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