1-Adamantanecarbonyl chloride → Decane

HRID 1683307Notes

Reaction equation

HRID 1683307 reaction equation
C([NH+]([CH2:6][CH3:7])CC)C.[C:8]12(C(Cl)=O)C[CH:12]3[CH2:13][CH:14](C[CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2>C(#N)C.N1C=CC=CC=1>[CH3:14][CH2:15][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 989151-Adamantanecarbonyl chlorideHCID 1385867Triethylammonium

Product 1

HCID 15600Decane

Reagents, catalysts & solvents 1

HCID 21959178Acetonitrile pyridineSolvent

Procedure

The dimethoxytrityl group of the derivatized CPG from Example 9 is removed by a treatment with 2% dichloroacetic acid followed by washing with dry acetonitrile. The CPG is washed with acetonitrile-pyridine (4:1) followed by a simultaneous treatment of the CPG with 20-30 equivalents of the 10-O-(dimethoxytrityl) decyl-phosphonic acid as the triethylammonium salt, 20-30 equivalents of adamantane carbonyl chloride in acetonitrile-pyridine. The mixture is agitated by circulating the reagents in the synthesis vessel for 10-15 minutes. The CPG is then briefly washed with acetonitrile-pyridine and then treated with diisopropyl phosphite adamantane carbonyl chloride to cap all unreacted hydroxyl groups. Finally, the CPG is washed with acetonitrile-pyridine and then acetonitrile. An estimate of coupling efficiency is derived from the treatment of the CPG with dichloracetic acid in acetonitrile followed by a measurement of the absorbance of an aliquot at 498 nm. Repeating the above procedure n times will yield an oligomer with n+1 decane units and n H-phosphonate linkages. The oligomer is tethered to a LCAA CPG by a succinate group as described above.

Workup

  1. customThe dimethoxytrityl group of the derivatized CPG from Example 9 is removed by a treatment with 2% dichloroacetic acid
  2. washby washing with dry acetonitrile
  3. washThe CPG is washed with acetonitrile-pyridine (4:1)
  4. customfor 10-15 minutes
  5. washThe CPG is then briefly washed with acetonitrile-pyridine
  6. additiontreated with diisopropyl phosphite adamantane carbonyl chloride
  7. customto cap all unreacted hydroxyl groups
  8. washFinally, the CPG is washed with acetonitrile-pyridine

Sources & evidence

ORD record
ord-daecc66bc5fa4f31acbb7a7964129b50
Source dataset
uspto-grants-1997_06
Patent number
US05637684

Reaction notes

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