Tetrabutylammonium Fluoride → HCID 131728525, compound

HRID 1695260Notes

Reaction equation

HRID 1695260 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:49])[C:22]1[CH:27]=[C:26]([CH3:28])[C:25](Br)=[C:24]([S:30]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[O:41][Si](C(C)(C)C)(C)C)(=[O:32])=[O:31])[CH:23]=1>O1CCCC1>[CH3:19][O:20][C:21]([C:22]1[CH:27]=[C:26]([CH3:28])[C:25]2[O:41][C:35]3[C:36]([Cl:40])=[CH:37][CH:38]=[CH:39][C:34]=3[CH2:33][S:30](=[O:32])(=[O:31])[C:24]=2[CH:23]=1)=[O:49]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67246667HCID 67246667, compound

Product 1

HCID 131728525HCID 131728525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of tetrabutyl ammonium fluoride (90 g, 0.283 mol) in tetrahydrofuran (250 mL) was added dropwise to a solution of compound of Example 1h (72 g, 0.135 mol) in tetrahydrofuran (350 mL) over a period of 25 min under nitrogen, at 5° C. The reaction mixture was stirred at 5° C. for 30 min. Solvent was removed under reduced pressure and water (250 mL) was added. The solid was filtered and washed with water (2000 mL). The crude product was purified by column chromatography (silica gel, methanol in chloroform) to obtain the title compound. Yield: 37.0 g (87%); 1H NMR (CDCl3, 300 MHz): δ 2.71 (s, 3H, CH3), 3.91 (s, 3H, OCH3), 4.72 (s, 2H, CH2), 7.25 (d, 1H, Ar), 7.33 (d, 1H, Ar), 7.45 (d, 1H, Ar), 8.09 (s, 1H, Ar), 8.46 (s, 1H, Ar); MS: m/e (El) 352 (M+).

Workup

  1. customSolvent was removed under reduced pressure and water (250 mL)
  2. additionwas added
  3. filtrationThe solid was filtered
  4. washwashed with water (2000 mL)
  5. customThe crude product was purified by column chromatography (silica gel, methanol in chloroform)

Sources & evidence

ORD record
ord-8232a9f219674c9184c75aa354d1aff5
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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