Tetrabutylammonium Fluoride Trihydrate → HCID 86756377, compound

HRID 634996Notes

Reaction equation

HRID 634996 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].C([Si](C)(C)[O:27][C@H:28]1[CH2:33][C@H:32]([O:34][Si](C(C)(C)C)(C)C)[CH2:31]/[C:30](=[CH:42]/[CH:43]=[CH:44]/[CH2:45][CH2:46][CH2:47][C:48]([CH3:63])([CH3:62])[CH2:49]/[CH:50]=[CH:51]/[C:52]([C:58]([F:61])([F:60])[F:59])([OH:57])[C:53]([F:56])([F:55])[F:54])/[C:29]1=[CH2:64])(C)(C)C>O1CCCC1>[F:54][C:53]([F:55])([F:56])[C:52]([C:58]([F:59])([F:60])[F:61])([OH:57])/[CH:51]=[CH:50]/[CH2:49][C:48]([CH3:63])([CH3:62])[CH2:47][CH2:46][CH2:45]/[CH:44]=[CH:43]/[CH:42]=[C:30]1\[C:29](=[CH2:64])[C@@H:28]([OH:27])[CH2:33][C@H:32]([OH:34])[CH2:31]\1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 86756378HCID 86756378, compound

Product 1

HCID 86756377HCID 86756377, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.83 g of tetrabutylammoniumfluoride trihydrate (2.60 mmol) in 3.5 ml of tetrahydrofuran was carefully dried by stirring during 2 h at room temperature over 1.05 g of 3 Å molecular sieve. This solution was then added to the above prepared 151 mg of (3E,10E)-12-[(Z)-(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-1,1,1-trifluoro-6,6-dimethyl-2-trifluoromethyl-dodeca-3,10-dien-2-ol and kept for 1.5 h at 45°. The reaction mixture was then poured onto crushed ice, extracted twice with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/ethylacetate=4/6) yielded 76 mg of the title compound as colourless oil.

Workup

  1. additionThis solution was then added to the
  2. waitkept for 1.5 h at 45°
  3. additionThe reaction mixture was then poured
  4. customonto crushed ice
  5. extractionextracted twice with ether
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-603c747e29e943bca6adf58222d92898
Source dataset
uspto-grants-2001_02
Patent number
US06184422B2

Reaction notes

Loading…