Ethyl Acetate → HCID 70237236, compound

HRID 651878Notes

Reaction equation

HRID 651878 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[I:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:30][CH2:31][O:32][C:33]([CH3:35])=[O:34]>C1C=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[CH2:20]([O:19][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([I:27])=[C:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:2][CH2:1][CH2:3][CH:30]=[CH:31][O:32][CH:33]2[CH2:35][CH2:18][CH2:9][CH2:10][O:34]2)[CH:18]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10457640HCID 10457640, compound

Product 1

HCID 70237236HCID 70237236, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 241BenzeneSolvent

Procedure

A solution of 80 (53 mg, 112 μmol) in benzene (5 mL) was added to a mixture of 50% aqueous NaOH (0.5 g) and benzyltributylammonium chloride (70 mg, 224 μmol, 2 equiv). The mixture was stirred vigorously for 15 min and 100 (147 mg, 556 μmol, 5 equiv) was added. The mixture was stirred vigorously for 12 h at 25° C. Ice-cold H2O (50 mL), and EtOAc (10 mL) were added. The aqueous layer was extracted with EtOAc (10 mL), the combined organic layers were dried (Na2SO4) and the solvent was removed under vacuum. Chromatography (SiO2, 2×20 cm, 10-25% EtOAc-hexane gradient elution) afforded 108 (58 mg, 72 mg theoretical, 80%) as an oil: 1H NMR (CDCl3, 400 MHz) δ 8.31 and 8.27 (two d, J=8.3, 8.8 Hz, 1H), 8.21 (d, J=8.2 Hz, 1H), 7.61-7.49 (m, 4H), 7.42-7.33 (m, 3H), 6.82-6.69 (m, 1H), 6.21 (m, 0.5H), 6.13 (d, 0.5H), 5.32-5.17 (m, 2H), 5.01 (dt, J=12.2, 7.5 Hz, 0.5H), 4.86 and 4.82 (two m, 1H), 4.41 (m, 0.5H), 3.81 (m, 2H), 3.51 (m, 1H), 3.36-3.21 (m, 1H), 2.12 and 1.92 (two m, 2H), 1.83-1.49 (m, 8H), 1.29 (s, 9H); IR (film) νmax 2940, 1699, 1591, 1407, 1366, 1338, 1158, 1099, 1037 cm−1.

Workup

  1. stirringThe mixture was stirred vigorously for 12 h at 25° C
  2. extractionThe aqueous layer was extracted with EtOAc (10 mL)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. customthe solvent was removed under vacuum
  5. washChromatography (SiO2, 2×20 cm, 10-25% EtOAc-hexane gradient elution)

Sources & evidence

ORD record
ord-6cf7cec374ed4fa5bc13e1b7b2ae2caa
Source dataset
uspto-grants-2001_08
Patent number
US06281354B1

Reaction notes

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