Tetrabutylammonium Fluoride → [6-[[2-(Trifluoromethyl)phenoxy]methyl]dithiin-3-yl]methanol

HRID 265313Notes

Reaction equation

HRID 265313 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:27])([F:26])[F:25])=[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]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:27])([F:26])[F:25])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 117436603-[(Tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin

Product 1

HCID 462632[6-[[2-(Trifluoromethyl)phenoxy]methyl]dithiin-3-yl]methanolYield 58%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the 3-[(tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin obtained above (70 mg, 0.16 mmol) in 2 mL THF was added a mixture of 1.0 mL of 1M tetrabutylammonium fluoride in THF and 0.6 mL of acetic acid. The reation mixture was stirred for 7 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 30 mg (58%) of the title compound; 1H NMR (CDCl3):δ7.60 (dd, J=8.0, J=l.6, 1 H), 7.50 (t, J=8.4, 1 H), 7.08 (t, J=8.0, 1 H), 6.99 (d, J=8.0 Hz, 1 H), 6.54 (d, J=6.0 Hz, 1 H), 6.44 (d, 1 H, J=6.0), 4.76 (s, 2 H), 4.30 (s, 2 H), 1.93 (bs, 1 H); 13C NMR (CDCl3):161.14, 135.73, 133.26, 128.84, 127.31 (q, J=5.4), 126.59, 125.06, 123.33, 120.90, 113.11, 69.45, 64.59; EI-MS:m/z 320.62.

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-fab5cd59d5aa49b9bbb2be74ce627349
Source dataset
uspto-grants-1997_07
Patent number
US05648354

Reaction notes

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