Tetrabutylammonium Fluoride → HCID 21024022, compound

HRID 1446627Notes

Reaction equation

HRID 1446627 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:22][CH:23]1[C:24]([O:68][CH:69]([O:71][CH2:72][CH3:73])[CH3:70])([CH3:67])[CH2:25][CH2:26][CH:27]([O:59][Si](C(C)(C)C)(C)C)[CH2:28][C:29]([O:31][CH:32](/[C:37](/[CH3:58])=[CH:38]/[CH:39]=[CH:40]/[CH:41]([CH3:57])[CH2:42][CH:43]2[O:56][CH:44]2[CH:45]([CH3:55])[CH:46]([O:49][CH:50]([O:52][CH2:53][CH3:54])[CH3:51])[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:68][CH:69]([O:71][CH2:72][CH3:73])[CH3:70])([CH3:67])[CH2:25][CH2:26][CH:27]([OH:59])[CH2:28][C:29]([O:31][CH:32](/[C:37](/[CH3:58])=[CH:38]/[CH:39]=[CH:40]/[CH:41]([CH3:57])[CH2:42][CH:43]2[O:56][CH:44]2[CH:45]([CH3:55])[CH:46]([O:49][CH:50]([O:52][CH2:53][CH3:54])[CH3:51])[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 Fluoride2×HCID 21024017HCID 21024017, compound

Product 1

HCID 21024022HCID 21024022, compoundYield 685.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A 1.0M solution of tetrabutylammonium fluoride (0.026 mmol) in tetrahydrofuran (0.026 mL, 0.026 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3-t-butyldimethylsiloxy-6,21-bis(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (19 mg, 0.024 mmol) in tetrahydrofuran (0.5 mL) at room temperature. The mixture was stirred at room temperature for 2 hours. Further, 0.026 mL of a 1.0M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.026 mL, 0.026 mmol) was added thereto at room temperature. After the reaction mixture was diluted with ethyl acetate, it was 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=70:30) to obtain the title compound (112 mg, 63%) as a colorless oil.

Workup

  1. customat room temperature
  2. washwas washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. 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=70:30)

Sources & evidence

ORD record
ord-9c7b9884b50740c19018009b6ab7c36c
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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