Potassium → HCID 11813000, compound

HRID 260397Notes

Reaction equation

HRID 260397 reaction equation
[C:1]1([O:7][C:8]([N:10]2[CH:23]([C:24]#[C:25]/[CH:26]=[CH:27]\[C:28]#[C:29][Si](C)(C)C)[C:22]3[CH2:21][CH2:20][CH2:19][C:18](=[O:34])[C:17]=3[C:16]3[CH:15]=[CH:14][C:13]([O:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:12][C:11]2=3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K]>C1COCC1.C(O)C.O.C(Cl)Cl.[N+]([O-])([O-])=O.[Ag+]>[C:1]1([O:7][C:8]([N:10]2[CH:23]([C:24]#[C:25]/[CH:26]=[CH:27]\[C:28]#[CH:29])[C:22]3[CH2:21][CH2:20][CH2:19][C:18](=[O:34])[C:17]=3[C:16]3[CH:15]=[CH:14][C:13]([O:35][C:36](=[O:41])[C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:12][C:11]2=3)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 5462222PotassiumHCID 10907882HCID 10907882, compound

Product 1

HCID 11813000HCID 11813000, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 6344DichloromethaneSolventHCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of Compound 211 (2.80 g, 4.95 mmol) in THF-EtOH-H2O (1:1:1, 300 mL) was added silver nitrate (3.36 g, 19.8 mmol) followed by stirring at 25° C. for one hour. Potassium cynide (2.26 g, 34.65 mmol) was added to the reaction mixture followed by stirring at 25° C. for another 10 minutes. The reaction mixture was diluted with CH2Cl2 (300 mL), washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 50 percent ethyl ether in petroleum ether) to furnish Compound 212 (2.20 g, 90 percent): Rf =0.43 (silica, 50 percent ethyl ether in petroleum ether); IR (CHCl3) νmax 3302, 2959, 1740 (shoulder), 1725 (shoulder), 1719, 1680, 1606, 1494, 1381, 1307, 1177, 1123 cm-1 ; 1H NMR (300 MHz, CDCl3 ) δ 8.25 (d, J=8.8 Hz, 1 H, H1), 7.50-7.17 (m, 6 H, H4and aromatic), 6.95 (dd, J=8.8, 1.1 Hz, 1 H, H2), 6.06 (s, 1 H, H6), 5.79 (s, 2 H, olefinic), 3.32 (d, J=1.0 Hz, 1 H, acetylenic), 2.86 (dt, J=18.9, 4.5 Hz, 1 H, H9), 2.76-2.51 (m, 3 H, H7 and H9), 2.23-2.16 (m, 2 H, H8), 1.33 (s, 9 H, COC(CH3)3); MS (FAB+) m/e (rel intensity) 626 (M+Cs, 16), 418 (13); HRMS for C31H27NO5Cs (M+Cs), calcd 626.0944, found 626.0975.

Workup

  1. stirringby stirring at 25° C. for another 10 minutes
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (silica gel, 50 percent ethyl ether in petroleum ether)

Sources & evidence

ORD record
ord-183d116d199b4a8fa11eddcb8b32364f
Source dataset
uspto-grants-1996_06
Patent number
US05527805

Reaction notes

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