Tetrabutylammonium Fluoride → HCID 21023989, compound

HRID 1446632Notes

Reaction equation

HRID 1446632 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-a89fcb28f9c04cb98a9b0827fd3eb757
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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