Acetonitrile → HCID 10389158, compound

HRID 721966Notes

Reaction equation

HRID 721966 reaction equation
[CH2:1]1[C:28]2=C(O)[C:24](=[CH:25][CH:26]=[CH:27]2)[CH2:23][C:20]2=[C:21]([OH:22])[C:16](=[CH:17][CH:18]=[CH:19]2)[CH2:15][C:11]2=[CH:12][CH:13]=[CH:14][C:9](=[C:10]2[OH:31])[CH2:8][C:4]2=[CH:5][CH:6]=[CH:7][C:2]1=[C:3]2O.[C:33](=[O:36])([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)([O:42][CH3:43])(=O)=O.[CH3:51]C#N>>[CH3:43][O:42][C:3]1[C:4]2=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:1][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:23][C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:15][C:11]4[C:10]([OH:31])=[C:9]([CH2:8]2)[CH:14]=[CH:13][CH:12]=4)[C:21]=3[O:22][CH3:51])[C:33]=1[OH:36]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 562409Calix[4]arene

Product 1

HCID 10389158HCID 10389158, compoundYield 98%

Procedure

A suspension of calix[4]arene (17.0 g, 40 mmole), anhydrous potassium carbonate (6.08 g, 44 mmole), and methyl tosylate (14.9 g, 80 mmole) were refluxed in CH3CN (500 mL) overnight. After evaporation of the solvent, the mixture was taken up in CH2Cl2 and washed with 1 N HCl and brine. The organic layer was dried with MgSO4 and the solvent was removed in vacuo to afford the product. It was recrystallized from CH3Cl/MeOH to yield white crystals (18.1 g, 98%). mp>300° C. dec. 1H NMR (500 MHz, CDCl3) δ: 7.76 (s, 2H), 7.08 (d, 4H, J=7.5 Hz), 6.88 (d, 4H, J=7.5 Hz), 6.73 (t, 2H, J=7.5 Hz), 6.68 (t, 2H, J=7.5 Hz), 4.31 (d, 4H, J=13.0 Hz), 3.99 (s, 6H), 3.41 (d, 4H, J=13.0 Hz). 13C NMR (125 MHz, CDCl3) δ: 153.2, 153.1, 132.9, 129.0, 128.5, 128.1, 125.3, 119.1, 63.7, 31.1.

Workup

  1. customAfter evaporation of the solvent
  2. washwashed with 1 N HCl and brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. customthe solvent was removed in vacuo
  5. customto afford the product
  6. customIt was recrystallized from CH3Cl/MeOH

Sources & evidence

ORD record
ord-808a8427dd00461b8ba528c2326f7a5d
Source dataset
uspto-grants-2006_11
Patent number
US07138075B2

Reaction notes

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