Tetrabutylammonium Fluoride → 2-Phenyl-1,3-dioxolane-2-methanol

HRID 1468756Notes

Reaction equation

HRID 1468756 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:12][CH2:11][CH2:10][O:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:13]1([C:8]2([CH2:7][OH:6])[O:12][CH2:11][CH2:10][O:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68160183HCID 68160183, compound

Product 1

HCID 126142482-Phenyl-1,3-dioxolane-2-methanolYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyldimethyl-(2-phenyl-[1,3]dioxolan-2-yl-methoxy)silane (5.5 g, 18.7 mmol) in tetrahydrofuran (50 ml) was added tetrabutylammonium fluoride (1M in tetrahydrofuran, 56 ml) at room temperature. The mixture was stirred at room temperature for 12 hours. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=3/1) to give (2-phenyl-[1,3]dioxolan-2-yl)methanol (1.54 g, 8.5 mmol, 45%) as a yellow oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-98d9baa0ab004de2880df39a0a1feb61
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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