Acetic Acid → HCID 86663414, compound

HRID 446493Notes

Reaction equation

HRID 446493 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.[F:23][C:24]([F:60])([F:59])[C:25]1[CH:26]=[C:27]([CH:52]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:54]=1)[C:28]([N:30]1[CH2:34][C@@:33]([CH2:42][CH2:43][O:44][Si](C(C)(C)C)(C)C)([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[O:32][CH2:31]1)=[O:29].C(OCC)(=O)C>O1CCCC1>[F:59][C:24]([F:23])([F:60])[C:25]1[CH:26]=[C:27]([CH:52]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:54]=1)[C:28]([N:30]1[CH2:34][C@@:33]([CH2:42][CH2:43][OH:44])([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[O:32][CH2:31]1)=[O:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86663415HCID 86663415, compound

Product 1

HCID 86663414HCID 86663414, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 508 mL) and acetic acid (70 mL, 1.27 mol) were added to a solution of the compound (131.76 g, 0.254 mol) obtained in Example 1b in tetrahydrofuran (500 mL), and the mixture was stirred at room temperature for 2 hours. Ethyl acetate (1000 mL) was added to the reaction mixture, washed with a saturated aqueous solution of sodium hydrogencarbonate, water, and saturated sodium chloride solution, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane, 30%→50%) to give the title compound (102.11 g; yield, 99%) as a colorless oily substance.

Workup

  1. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water, and saturated sodium chloride solution
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane, 30%→50%)

Sources & evidence

ORD record
ord-20864cf5976f4c7d969d28bdff9c4626
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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