4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 6-(3-adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl ester

HRID 733655Notes

Reaction equation

HRID 733655 reaction equation
[O:1]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([C:27]45[CH2:36][CH:31]6[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]6)[CH2:28]4)[CH2:34]5)[CH:20]=3)[CH:15]=2)[CH:10]=1)[Si](C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCN(C(C)C)C(C)C.[C:64]1([CH3:74])[CH:69]=[CH:68][C:67]([S:70](Cl)(=[O:72])=[O:71])=[CH:66][CH:65]=1>C1COCC1.CCOC(C)=O.CN(C1C=CN=CC=1)C>[C:27]12([C:21]3[CH:20]=[C:19]([C:14]4[CH:15]=[C:16]5[C:11](=[CH:12][CH:13]=4)[CH:10]=[C:9]([O:1][S:70]([C:67]4[CH:68]=[CH:69][C:64]([CH3:74])=[CH:65][CH:66]=4)(=[O:72])=[O:71])[CH:18]=[CH:17]5)[CH:24]=[CH:23][C:22]=3[O:25][CH3:26])[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 598563162-Tert-butyl-dimethylsiloxy-6-(3-adamantan-1-yl-4-methoxyphenyl)-naphthalene

Product 1

HCID 59856317Toluene-4-sulfonic acid 6-(3-adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-tert-butyl-dimethylsiloxy-6-(3-adamantan-1-yl-4-methoxyphenyl)-naphthalene (14 g, 28 mmol) in THF (160 ml) was added TBAF (28 ml, 28 mmol) and the reaction stirred at RT for 5 min. The reaction mixture was diluted with EtOAc and washed with 1N HCl, brine, and dried over Na2SO4. The crude product was concentrated in vacuo and the residue was dissolved in DCM (200 ml). DMAP (0.2 equiv), DIEA (1.2 equiv) and toluene-4-sulfonyl chloride (1 equiv) were added and the reaction was stirred at RT for 30 minutes. The solvent was removed, the residue was dissolved in EtOAc, washed with 1N HCl, brine, and dried over Na2SO4. The solvent was removed and the crude product was recrystallized from acetonitrile.

Workup

  1. washwashed with 1N HCl, brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe crude product was concentrated in vacuo
  4. dissolutionthe residue was dissolved in DCM (200 ml)
  5. stirringthe reaction was stirred at RT for 30 minutes
  6. customThe solvent was removed
  7. dissolutionthe residue was dissolved in EtOAc
  8. washwashed with 1N HCl, brine
  9. dry with materialdried over Na2SO4
  10. customThe solvent was removed
  11. customthe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-429713fb369e4801a7238473167de570
Source dataset
uspto-grants-2009_09
Patent number
US07589239B2

Reaction notes

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