Tetrabutylammonium Fluoride → HCID 67246085, compound

HRID 1695273Notes

Reaction equation

HRID 1695273 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:47])[C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([S:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[O:39][Si](C(C)(C)C)(C)C)[CH:23]=1>C1COCC1>[CH3:19][O:20][C:21](=[O:47])[C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([S:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[OH:39])[CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67246220HCID 67246220, compound

Product 1

HCID 67246085HCID 67246085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The solution of tetrabutyl ammonium fluoride (42.8 g, 0.13 mol) in THF (350 mL) was added dropwise to a solution of compound of Example 1g (35 g, 0.068 mol) in THF (150 mL) under nitrogen at 5° C. and stirred for 30 min. Solvent was removed from the reaction mixture and ice water (200 mL) was added. The solid separated was filtered, and washed with water (3×100 ml). The crude obtained was purified by column chromatography (silica gel, ethyl acetate/pet. ether) to obtain the title compound. Yield: 24 g, (88%); 1H NMR (CDCl3, 300 MHz): δ 2.44 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 4.26 (s, 2H, CH2), 6.81 (t, 1H, Ar), 7.20-7.26 (m, 2H, Ar), 6.81 (t, 1H, Ar), 7.70 (s, 1H, Ar); MS: m/e (El) 401 (M+).

Workup

  1. customSolvent was removed from the reaction mixture and ice water (200 mL)
  2. additionwas added
  3. customThe solid separated
  4. filtrationwas filtered
  5. washwashed with water (3×100 ml)
  6. customThe crude obtained
  7. customwas purified by column chromatography (silica gel, ethyl acetate/pet. ether)

Sources & evidence

ORD record
ord-f1fb28803b9142749d59850b765ce965
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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