Tetrabutylammonium Fluoride → HCID 462629, compound

HRID 265311Notes

Reaction equation

HRID 265311 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]=[C:20]([N:24]([CH3:26])[CH3:25])[CH:19]=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]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]([CH3:26])[CH3:25])[CH:19]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10047132HCID 10047132, compound

Product 1

HCID 462629HCID 462629, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the 3-[(tert-butyldimethylsilyloxy)methyl]-6-[[3-(N,N-dimethylamino)-phenyloxy]methyl]-1,2-dithiin obtained above (100 mg, 0.24 mmol) in 2 mL THF was added a mixture of 2.4 mL of 1M tetrabutylammonium fluoride in THF and 1.4 mL of acetic acid. The reation mixture was stirred for 3 h until TLC analysis showed the reaction to be complete, then concentrated in vacuo. The residue was partitioned between 40 mL of water and 60 mL 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 chromatographed over silica gel column (ethyl acetate-hexane, 1:1) to yield 60.5 mg (84.0%) of the title compound. Further purification was accomplished by reverse-phase HPLC (PRP-1 column, acetonitrile-water, 2:3); 1H-NMR (CDCl3) δ7.3 (bs, 1 H), 7.1 (bs, 1 H), 6.64 (s, 1 H), 6.55 (d, J=7.2, 1 H), 6.46(d, J=5.6, 1 H), 6.41 (d, J=5.6, 1 H), 4.65 (s, 2 H), 4.30 (s, 2 H), 2.69 (s, 6 H).

Workup

  1. additionwas added
  2. customthe reaction
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between 40 mL of water and 60 mL 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 chromatographed over silica gel column (ethyl acetate-hexane, 1:1)

Sources & evidence

ORD record
ord-f426a062e10e4afcb31388ae8a93d8ec
Source dataset
uspto-grants-1997_07
Patent number
US05648354

Reaction notes

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