t-Butylammonium fluoride → HCID 56590408, compound

HRID 2406859Notes

Reaction equation

HRID 2406859 reaction equation
C([Si]([O:8][C@H:9]1[CH2:13][CH2:12][C:11]([C:14]([CH3:16])=[CH2:15])=[CH:10]1)(C)C)(C)(C)C.[F-].C([NH3+])(C)(C)C>C1COCC1>[C:14]([C:11]1[CH2:12][CH2:13][C@H:9]([OH:8])[CH:10]=1)([CH3:16])=[CH2:15]

Participants

4

Reactant 2

HCID 21866379t-Butylammonium fluorideHCID 57386254HCID 57386254, compound

Product 1

HCID 56590408HCID 56590408, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound (6a) (402.8 mg; 1.689 mmol) in THF (34 mL) was cooled to 0° C. and treated with 1.0 M tert-Butylammonium floride (2.55 mL, 2.55 mmol). The next 3½ hours the reaction mixture was stirred at room temperature and then quenched with saturated aqueous NH4Cl. The resulting solution was extracted with DCM (3×) and AcOEt (1×), dried (Na2SO4) and concentrated in vacuo. Purification by chromatography (pentane/ether 3/1 to 2/1) provided 190.4 mg of compound (7a) as clear yellow oil with 95% yield.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionThe resulting solution was extracted with DCM (3×) and AcOEt (1×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (pentane/ether 3/1 to 2/1)

Sources & evidence

ORD record
ord-ba28796811c740358b8dcd8e8414e55e
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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