1,1'-Carbonyldiimidazole → HCID 70298427, compound

HRID 1106902Notes

Reaction equation

HRID 1106902 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][C:11]([OH:13])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26]([O:33][C:34]1[CH:35]=[C:36]([CH:40]([NH:55][CH3:56])[CH2:41][N:42]2[CH2:46][CH2:45][CH:44]([O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[CH2:43]2)[CH:37]=[CH:38][CH:39]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH:5]1[O:1][C:2]([CH2:10][C:11]([N:55]([CH:40]([C:36]2[CH:37]=[CH:38][CH:39]=[C:34]([O:33][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:35]=2)[CH2:41][N:42]2[CH2:46][CH2:45][CH:44]([O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:49])[CH3:50])[CH2:43]2)[CH3:56])=[O:13])=[C:3]2[CH:4]=[CH:9][CH:8]=[CH:7][C:6]=12

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 111058882-(1-Benzofuran-2-yl)acetic acidHCID 70299913HCID 70299913, compound

Product 1

HCID 70298427HCID 70298427, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-benzofuran acetic acid (1.446 g, 8.01 mmol) in THF (5 mL) at room temperature was added carbonyldiimidazole (1.31 g, 8.09 mmol). After stirring for 2 hours, a solution of Example 5 (2.68 g, 6.09 mmol) in THF (10 mL) was added. After stirring for 16 hours, all volatiles were removed in vacuo and the residue dissolved in ethyl acetate (300 mL). This solution was washed with saturated sodium hydrogencarbonate solution, then water, then saturated NaCl solution (50 mL of each). After drying (MgSO4) and concentration in vacuo, column chromatography (60:40 ethyl acetate:heptane) gave the desired product, 3.04 g, 83%.

Workup

  1. stirringAfter stirring for 16 hours
  2. customall volatiles were removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate (300 mL)
  4. washThis solution was washed with saturated sodium hydrogencarbonate solution
  5. customAfter drying
  6. concentration(MgSO4) and concentration in vacuo, column chromatography (60:40 ethyl acetate:heptane)

Sources & evidence

ORD record
ord-c0319dfd30e24f52b491769b8cfcd142
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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