TBAF tetrahydrofuran → HCID 67543090, compound

HRID 885464Notes

Reaction equation

HRID 885464 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12]1([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:20]2[C:15](=[CH:16][C:17]([C:21]#[N:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OC(=O)C)C>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C:20]2[C:15](=[CH:16][C:17]([C:21]#[N:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1

Participants

5

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 67545393HCID 67545393, compound

Product 1

HCID 67543090HCID 67543090, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

34.1 g (80.8 mmol) of the 1-(3-tert-butyldimethylsilyloxypropyl)-1-(4-methoxyphenyl)-1,3-dihydro-5-isobenzofurancarbonitrile prepared in step 4 was dissolved in 200 ml of tetrahydrofuran. 121.1 ml (121.1 mmol) of 1 M tetrabutylammonium fluoride tetrahydrofuran was added dropwise to the solution at room temperature, and the mixture was stirred for 2 hrs. The reaction mixture was diluted in ethylacetate, and washed with water and saturated NaCl solution. An organic layer was dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified using column chromatography to afford 15.0 g of the pale yellow target compound (yield: 60%).

Workup

  1. washwashed with water and saturated NaCl solution
  2. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-04a7115869fc4985b8ae20807c435597
Source dataset
uspto-grants-2012_08
Patent number
US08242159B2

Reaction notes

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