Acetic Acid → t-Butyl 4-[2-(2-cyano-3-methoxy-2-cyclopentenyl)ethyl]benzoate

HRID 742306Notes

Reaction equation

HRID 742306 reaction equation
[C:1]([CH:3]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:23])#[N:2].[CH:24](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.C(#N)C.CCCCCC>[C:1]([C:3]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[CH:21][CH:22]=2)[CH2:6][CH2:5][C:4]=1[O:23][CH3:24])#[N:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 10470833t-Butyl 4-(2-(2-cyano-1-cyclopentanon-3-yl)ethyl]benzoate

Product 1

HCID 10359093t-Butyl 4-[2-(2-cyano-3-methoxy-2-cyclopentenyl)ethyl]benzoate

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21959252Acetonitrile methanolSolvent

Procedure

t-Butyl 4-[2-(2-cyano-1-cyclopentanon-3-yl)ethyl]benzoate (0.43 g, 1.37 mmol) prepared in the Preparative Example 105 and N,N-diisopropylethylamine (0.21 g, 1.64 mmol) were dissolved in a methanol/acetonitrile (1:5) mixture, followed by the addition of 3.2 g of a 10% by weight solution of trimethylsilyldiazomethane in hexane. The obtained mixture was stirred at room temperature for 2 hours, followed by the addition of a small amount of acetic acid. The mixture this obtained was stirred and distilled to remove the solvent. The residue was dissolved in diethyl ether, washed with diluted hydrochloric acid, dilute alkali ind an aqueous solution of common salt, dehydrated and concentrated to dryness. The residue was purified by silica gel column chromatography to give the objective compound. yield: 0.23 g

Workup

  1. stirringThe mixture this obtained was stirred
  2. distillationdistilled
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washwashed with diluted hydrochloric acid
  6. additiondilute alkali
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by silica gel column chromatography
  9. customto give the objective compound

Sources & evidence

ORD record
ord-3d3efd8cadab42c9932974d06b2633a1
Source dataset
uspto-grants-1996_09
Patent number
US05554615

Reaction notes

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