Ethyl 4-(4-nitrophenoxy)cyclohexanecarboxylate → HCID 178472465, compound

HRID 1713832Notes

Reaction equation

HRID 1713832 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>CCO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:20][CH:21]=1

Participants

5

Reactant 1

HCID 57435335Ethyl 4-(4-nitrophenoxy)cyclohexanecarboxylate

Product 1

HCID 178472465HCID 178472465, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium (10 wt. %) on carbon (50 mg) was added in one portion to a solution of crude ethyl 4-(4-nitrophenoxy)cyclohexanecarboxylate in a mixture of EtOH (15 mL) and THF (10 mL). The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 16 h then filtered and concentrated in vacuo to give a solid that was purified by chromatography, using 30-60% EtOAc in isohexane as eluent, to give the title compound (127 mg, 4% over 2 steps) as a solid; 1H NMR (CDCl3) δ1.16-1.20 (3H, t), 1.31-1.42 (2H, m), 1.43-1.52 (2H, m), 1.96-2.01 (2H, m), 2.05-2.10 (2H, m), 2.20-2.28 (1H, m), 3.35 (2H, br s), 3.89-3.96 (1H, m), 4.05 (2H, q), 6.53-6.57 (2H, d), 6.65-6.69 (2H, d); MS m/e MH+ 264.

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated in vacuo
  3. customto give a solid
  4. customthat was purified by chromatography

Sources & evidence

ORD record
ord-561705281a9d4654ad58b7339b45ad57
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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