Tetrahydrofuran → HCID 57915012, compound

HRID 931842Notes

Reaction equation

HRID 931842 reaction equation
Br[CH2:2][C:3]([CH2:5][O:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH2:4].C[Si]([C:30]#[N:31])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>CC#N>[C:8]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:6][CH2:5][C:3](=[CH2:4])[CH2:2][C:30]#[N:31])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 57915015HCID 57915015, compound

Product 1

HCID 57915012HCID 57915012, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 11 (1.45 g; 3.69 mmol) and in dry CH3CN (37 mL) was added trimethylsilyl cyanide (0.49 mL; 3.69 mmol). Then 1 M tetrabutylammonium fluoride (TBAF) in THF solution (3.69 mL, 3.69 mmol) was added slowly at room temperature and the reaction was stirred for 20 min. Most solvents were evaporated and ethyl acetate (100 mL) and saturated aqueous NaHCO3 (30 mL) were added. The organic layer was washed by saturated aqueous NaCl and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by flash column chromatography over silica gel using acetate-hexane (1:10) as the eluent to afford 12 as white solid (1.01 g; 64% yield): 1H NMR (400 MHz, CDCl3) δ 7.39-7.45 (m, 6H, six of ArH), 7.21-7.34 (m, 9H, nine of ArH), 5.31 (s, 2H, C═CH2), 3.64 (s, 2H, Ph3COCH2), 3.11 (s, 2H, CH2CN); 13C NMR (100 MHz, CDCl3) δ 143.3, 135.5, 128.2, 127.7, 126.9, 116.8, 114.7, 87.0, 65.7, 21.9, (10).

Workup

  1. customMost solvents were evaporated
  2. additionethyl acetate (100 mL) and saturated aqueous NaHCO3 (30 mL) were added
  3. washThe organic layer was washed by saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-ba2a17e7e1f54c14adfac9c569e5906d
Source dataset
uspto-grants-2016_03
Patent number
US09297042B2

Reaction notes

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