Pyridinium → HCID 85303357, compound

HRID 1489471Notes

Reaction equation

HRID 1489471 reaction equation
CC([Si](C)(C)[O:6][CH:7]([C:9]#[C:10][CH2:11][CH:12]([O:61][Si:62]([C:75]([CH3:78])([CH3:77])[CH3:76])([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([O:43][Si:44]([C:57]([CH3:60])([CH3:59])[CH3:58])([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:30][C:31]#[C:32][CH:33]([O:35][Si](C(C)(C)C)(C)C)[CH3:34])=[CH:20][CH:19]=1)[CH3:8])(C)C.[NH+]1C=CC=CC=1>C(O)C>[CH3:58][C:57]([Si:44]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[O:43][CH:29]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([O:61][Si:62]([C:75]([CH3:76])([CH3:77])[CH3:78])([C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH2:11][C:10]#[C:9][CH:7]([OH:6])[CH3:8])=[CH:19][CH:20]=1)[CH2:30][C:31]#[C:32][CH:33]([OH:35])[CH3:34])([CH3:60])[CH3:59]

Participants

4

Reactant 2

HCID 4989215PyridiniumHCID 86751408HCID 86751408, compound

Product 1

HCID 85303357HCID 85303357, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of the alkyne 12b (526 mg, 457 μmol) in absolute ethanol (6.0 mL) was added pyridinium p-toluenesulfanate (273 mg, 1.09 mmol) in one portion. The reaction mixture was stirred at 55° C. overnight (~14 h). The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (50 mL). The organic solution was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by MPLC (3:1 hexane:ethyl acetate) to give the alcohol 14 (387 mg, 92%); IR (neat, thin layer): 3405, 3070, 3048, 2935, 2858, 1963, 1893, 1827, 1589, 1507, 1471, 1428, 1365, 1228, 1155, 1002, and 823 cm-1 ; Anal. Calcd for C58 H74O6Si2 : C, 75.44%; H, 8.08%. Found: C, 75.16%; H, 7.89%; tlc: Rf =0.14 in 3:1 hexane:ethyl acetate; [α]DRT =-7.9°, c=5.47 in ethyl acetate.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washThe organic solution was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by MPLC (3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2b4357bc35184499b765a2e7b3be4cbe
Source dataset
uspto-grants-1997_10
Patent number
US05677467

Reaction notes

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