Tetrabutylammonium Fluoride → HCID 462634, compound

HRID 265314Notes

Reaction equation

HRID 265314 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]1[S:9][S:10][C:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2CF)=[CH:12][CH:13]=1)(C)(C)C.[F-:26].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(O)(=O)C>[OH:6][CH2:7][C:8]1[S:9][S:10][C:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:26])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19033989HCID 19033989, compound

Product 1

HCID 462634HCID 462634, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the 3-[(tert-butyldimethyl-silyloxy)methyl]-6-[(2fluoromethylphenyloxy)methyl]-1,2-dithiin obtained above (250 mg, 0.65 mmol) in 5 mL THF was added a mixture of 3.0 mL of 1M tetrabutylammonium fluoride in THF and 2.0 mL of acetic acid. The reation mixture was stirred for 5 h until TLC analysis showed the reaction to be complete, then concentrated in vacuo. The residue was partitioned between 20 mL of water and 20 mL ethyl acetate. The organic phase was washed with 3% solution of aqueous sodium bicarbonate (50 mL), water, dried over sodium sulfate, and then concentrated to a small volume. The residue was purified by silica gel chromatography (ethyl acetate-hexane, 1:3) to yield 120 mg (68%) of the title compound; 1H NMR (CDCl3):δ7.12-6.9 (m, 4 H), 6.47 (d, J=6.0, 1 H), 6.39 (d, J=6.0, 1 H), 4.74 (s, 2 H), 4.28 (s, 2 H); MS (EI) 270.1 (M+).

Workup

  1. additionwas added
  2. customthe reaction
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between 20 mL of water and 20 mL ethyl acetate
  5. washThe organic phase was washed with 3% solution of aqueous sodium bicarbonate (50 mL), water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a small volume
  8. customThe residue was purified by silica gel chromatography (ethyl acetate-hexane, 1:3)

Sources & evidence

ORD record
ord-5d29db4ac7844c028b165ef80562c24b
Source dataset
uspto-grants-1997_07
Patent number
US05648354

Reaction notes

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