Tetrabutylammonium Fluoride → HCID 178499946, compound

HRID 516897Notes

Reaction equation

HRID 516897 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:57]=[CH:56][C:30]([CH2:31]/[C:32](=[C:37](\[C@H:42]2[CH2:47][CH2:46][C@@H:45]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[CH2:44][CH2:43]2)/[C:38]([O:40][CH3:41])=[O:39])/[C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>C1COCC1>[Si:49]([O:48][C@@H:45]1[CH2:46][CH2:47][C@H:42](/[C:37](=[C:32](\[CH2:31][C:30]2[CH:29]=[CH:28][C:27]([OH:26])=[CH:57][CH:56]=2)/[C:33]([O:35][CH3:36])=[O:34])/[C:38]([O:40][CH3:41])=[O:39])[CH2:43][CH2:44]1)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178499986HCID 178499986, compound

Product 1

HCID 178499946HCID 178499946, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M tetrabutyl ammonium fluoride solution in THF (0.29 ml, 0.29 mmol) was added dropwise to a solution of dimethyl 2-(4-((tert-butyldimethylsilyl)oxy)benzyl)-3-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)maleate (55 mg, 0.10 mmol) in THF (1.0 ml) at 0° C., and the mixture was stirred at room temperature for 5 hr. The solvent was removed by distillation under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate=85:15) to give the title compound as a yellow oil (35 mg, yield 80%).

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. customthe residue was chromatographed on silica gel column (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-578b7962348e4d98b87ec24ebe7f327e
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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