Tetrabutylammonium Fluoride → HCID 178488929, compound

HRID 265317Notes

Reaction equation

HRID 265317 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([C:16]2[C:25]([O:26][Si](C(C)(C)C)(C)C)=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:34][CH3:35])[N:17]=2)=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(O)(=O)C>[OH:8][CH2:9][C:10]1[S:11][S:12][C:13]([C:16]2[C:25]([OH:26])=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:34][CH3:35])[N:17]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19033992HCID 19033992, compound

Product 1

HCID 178488929HCID 178488929, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the 3-[(tert-butyldimethylsilyloxy)methyl]-6-[methyloxy[3-(tert-butyldimethylsilyloxy)quinoxalin-2-yl]]-1,2-dithiin obtained above (50 mg, 0.09 mmol) in 1 mL of THF was added a mixture of 1.2 mL of 1M tetrabutylammonium fluoride in THF and 0.7 mL of acetic acid. The reation mixture was stirred for 3 h until TLC analysis showed the reaction to be complete, and then concentrated in vacuo. The residue was partitioned between 20 mL of water and 30 mL of ethyl acetate. The organic phase was washed with dilute aqueous sodium bicarbonate, water, dried over sodium sulfate, and then evaporated to a small volume. The residue was purified by flash chromatography (ethyl acetate-hexane, 1:1) to yield 15 mg (51.7%) of the title compound. Further purification was accomplished by reverse phase HPLC (acetonitrile:water 1:1, PRP-1 column); 1H-NMR (CD3OD) 5.68 (d, J=8.0, 1 H), 7.47 (m, 2 H), 7.37 (m, 1 H), 6.66 (d, J=5.6, 1 H), 6.42 (d, J=6.0, 1 H), 5.16 (s, 2 H), 4.17 (s, 2 H); MS (EI) 319.1 (M+).

Workup

  1. additionwas added
  2. customthe reaction
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between 20 mL of water and 30 mL of ethyl acetate
  5. washThe organic phase was washed with dilute aqueous sodium bicarbonate, water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to a small volume
  8. customThe residue was purified by flash chromatography (ethyl acetate-hexane, 1:1)

Sources & evidence

ORD record
ord-bd2058dc52f64918bc1d03fddf176f67
Source dataset
uspto-grants-1997_07
Patent number
US05648354

Reaction notes

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