Tetrabutylammonium Fluoride → HCID 131728431, compound

HRID 1172464Notes

Reaction equation

HRID 1172464 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:47])[C:22]1[CH:27]=[CH:26][C:25](Br)=[C:24]([S:29]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:39][Si](C(C)(C)C)(C)C)(=[O:31])=[O:30])[CH:23]=1>C1COCC1>[CH3:19][O:20][C:21]([C:22]1[CH:27]=[CH:26][C:25]2[O:39][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH2:32][S:29](=[O:31])(=[O:30])[C:24]=2[CH:23]=1)=[O:47]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68424964HCID 68424964, compound

Product 1

HCID 131728431HCID 131728431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetra-n-butylammonium fluoride (0.693 g, 2.2 mol) in THF (15 mL) was added dropwise to a solution of Example 1g (0.55 g, 1.1 mmol) in dry THF (5 mL) at 0° C. The reaction mixture was stirred for 1 h and treated with crushed ice to obtain the title compound as a solid. It was filtered, washed with water and dried. Yield: 0.25 g, (75%); 1H NMR (CDCl3): δ 3.90 (s, 3H, OCH3), 4.60 (s, 2H, CH2), 7.30-7.40 (m, 5H, Ar), 8.20 (d, 1H, Ar), 8.60 (d, 1H, Ar); MS: m/e (EI+) 304 (M+).

Workup

  1. additiontreated with crushed ice

Sources & evidence

ORD record
ord-175dc81ce2d042dd81621fca2228a47d
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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