Ethyl Acetate → HCID 57841185, compound

HRID 883084Notes

Reaction equation

HRID 883084 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:17][NH:16][N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:28]1(I)[CH2:32][CH2:31][CH2:30][CH2:29]1.CCOC(C)=O>CN(C)C=O>[CH:28]1([N:16]2[CH:17]=[C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:13][CH:12]=3)=[N:15]2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 73784IodocyclopentaneHCID 178450770HCID 178450770, compound

Product 1

HCID 57841185HCID 57841185, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To tert-Butyl 3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxylate (156 mg, 0.46 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride, 60% in mineral oil (20.8 μg, 0.52 mmol). After the gas evolution ceased (about 5 minutes), cyclopentyl iodide (59 μL, 0.51 mmol) was added dropwise and the mixture was stirred for 16 hours at room temperature. EtOAc was added and the crude mixture was washed with a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with EtOAc (3 times). The combined organic extracts were washed with water and brine. The organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with petroleum ether/DCM) to afford the title compound as a white solid (0.131 g, 69% yield). MS (ES+) m/e=405. 1H NMR (CDCl3) δH 1.51 (9H, s), 1.70-1.80 (2H, m), 1.85-2.00 (2H, m), 2.02-2.13 (2H, m), 2.18-2.30 (2H, m), 4.71 (1H, quint.), 7.06 (4H, d), 7.12 (1H, t), 7.35 (2H, t), 7.76 (2H, d), 7.95 (1H, s).

Workup

  1. additionwas added dropwise
  2. washthe crude mixture was washed with a saturated aqueous solution of NaHCO3
  3. extractionThe aqueous phase was further extracted with EtOAc (3 times)
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialThe organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (eluting with petroleum ether/DCM)

Sources & evidence

ORD record
ord-3eac9fa884c042d3aa312bd0cd19dfb6
Source dataset
uspto-grants-2012_08
Patent number
US08236832B2

Reaction notes

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