Tetrabutylammonium Fluoride Trihydrate → HCID 86756379, compound
Reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].C([Si](C)(C)[O:27][C@@H:28]1[CH2:33][C:32](=[CH:34]/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][C:40]([CH3:59])([CH3:58])[CH2:41]/[CH:42]=[CH:43]/[C:44]([C:54]([F:57])([F:56])[F:55])([O:49][Si](C)(C)C)[C:45]([F:48])([F:47])[F:46])[CH2:31][C@@H:30]([O:60][Si](C(C)(C)C)(C)C)[CH2:29]1)(C)(C)C>O1CCCC1>[F:46][C:45]([F:47])([F:48])[C:44]([C:54]([F:55])([F:56])[F:57])([OH:49])/[CH:43]=[CH:42]/[CH2:41][C:40]([CH3:59])([CH3:58])[CH2:39][CH2:38][CH2:37]/[CH:36]=[CH:35]/[CH:34]=[C:32]1[CH2:33][C@@H:28]([OH:27])[CH2:29][C@H:30]([OH:60])[CH2:31]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1.40 g of tetrabutylammoniumfluoride trihydrate (4.45 mmol) in 6 ml of tetrahydrofuran was carefully dried by stirring during 2 h at room temperature over 1.78 g of 3 Å molecular sieve. This solution was then added to the above prepared 270 mg of (1R,3R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-((2E,9E)-12,12,12-trifluoro-7,7-dimethyl-11-trifluoromethyl-11-trimethylsilanyloxy-dodeca-2,9-dienylidene)-cyclohexane (0.371 mmol) and kept for 1.5 h at 40°. The reaction mixture was then poured onto crushed ice/NH4Cl, extracted twice with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/ethylacetate=25/75) yielded 165 mg of the title compound as colourless oil. Typically, this product is contaminated with small amounts of 2Z-isomer which can be removed by HPLC.
Workup
- additionThis solution was then added to the
- waitkept for 1.5 h at 40°
- additionThe reaction mixture was then poured
- extractionextracted twice with ether
- washwashed with water
- dry with materialdried over sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-9438c7cdf3144d05b875bb1f03511584
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06184422B2
Reaction notes
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