Tetrabutylammonium Fluoride → HCID 178521541, compound

HRID 2368129Notes

Reaction equation

HRID 2368129 reaction equation
C([Si]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[O:26][C:27]3[CH:33]=[C:32]([O:34][CH2:35][CH:36]4[CH2:38][CH2:37]4)[CH:31]=[CH:30][C:28]=3[CH:29]=2)[CH2:21][CH2:20]1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:36]1([CH2:35][O:34][C:32]2[CH:31]=[CH:30][C:28]3[CH:29]=[C:25]([C@H:22]4[CH2:23][CH2:24][C@H:19]([OH:18])[CH2:20][CH2:21]4)[O:26][C:27]=3[CH:33]=2)[CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67448165HCID 67448165, compound

Product 1

HCID 178521541HCID 178521541, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of a solution of tert-butyl({4-[6-(cyclopropylmethoxy)-1-benzofuran-2-yl]cyclohexyl}oxy)diphenylsilane (3.36 g) and tetrabutylammonium fluoride in THF (1.0 M, 12.8 mL) in THF (30 mL) was stirred at room temperature overnight and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (0.66 g).

Workup

  1. extractionextracted with ethyl acetate and water
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-112c69f14d59445f9e0beb8310d68374
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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