Tetrabutylammonium Fluoride → HCID 21023989, compound

HRID 1795682Notes

Reaction equation

HRID 1795682 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:22][CH:23]1[C:24]([O:69][CH:70]([O:72][CH2:73][CH3:74])[CH3:71])([CH3:68])[CH2:25][CH2:26][CH:27]([O:60][Si](C(C)(C)C)(C)C)[CH2:28][C:29]([O:31][CH:32](/[C:37](/[CH3:59])=[CH:38]/[CH:39]=[CH:40]/[CH:41]([CH3:58])[CH2:42][CH:43]2[O:57][CH:44]2[CH:45]([CH3:56])[CH:46]([O:49][C:50](=[O:55])[CH2:51][O:52][CH2:53][CH3:54])[CH2:47][CH3:48])[CH:33]([CH3:36])[CH:34]=[CH:35]1)=[O:30])(=[O:21])[CH3:20]>O1CCCC1.C(OCC)(=O)C>[C:19]([O:22][CH:23]1[C:24]([O:69][CH:70]([O:72][CH2:73][CH3:74])[CH3:71])([CH3:68])[CH2:25][CH2:26][CH:27]([OH:60])[CH2:28][C:29]([O:31][CH:32](/[C:37](/[CH3:59])=[CH:38]/[CH:39]=[CH:40]/[CH:41]([CH3:58])[CH2:42][CH:43]2[O:57][CH:44]2[CH:45]([CH3:56])[CH:46]([O:49][C:50](=[O:55])[CH2:51][O:52][CH2:53][CH3:54])[CH2:47][CH3:48])[CH:33]([CH3:36])[CH:34]=[CH:35]1)=[O:30])(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21024015HCID 21024015, compound

Product 1

HCID 21023989HCID 21023989, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.037 mL, 0.037 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3-t-butyldimethylsiloxy-21-ethoxyacetoxy-6-(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (15 mg, 0.018 mmol) in tetrahydrofuran (1 mL) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crude product was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 100 μm, eluate; hexane:ethyl acetate=50:50) to obtain the title compound (8.8 mg, 68%) as a colorless oil.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting crude product was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 100 μm, eluate; hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-bdba1fd7e9af4f3eafa8ae8f5ba3c547
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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