Tetrabutylammonium Fluoride → HCID 178521554, compound

HRID 2368138Notes

Reaction equation

HRID 2368138 reaction equation
[Si]([O:18][C@H:19]1[CH2:24][CH2:23][C@H: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[N:29]=2)[CH2:21][CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[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[N: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 178455541HCID 178455541, compound

Product 1

HCID 178521554HCID 178521554, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of a solution (1.0 M, 2.72 mL) of 2-(trans-4-{[tert-butyl(diphenyl)silyl]oxy}cyclohexyl)-6-(cyclopropylmethoxy)-1,3-benzoxazole (714 mg) and tetrabutylammonium fluoride in THF in THF (5 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 (311 mg).

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-56da039a62094470b541c4689362cfd4
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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