Tetrabutylammonium Fluoride → HCID 58444042, compound

HRID 60721Notes

Reaction equation

HRID 60721 reaction equation
[CH3:1][C:2]1([CH3:29])[O:6][C@@H:5]2[O:7][C@H:8]([CH2:10][O:11][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:9][C@@H:4]2[O:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][C:2]1([CH3:29])[O:6][C@@H:5]2[O:7][C@H:8]([CH2:10][OH:11])[CH2:9][C@@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 72707693[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methoxy-tert-butyl-diphenyl-silane2×

Product 1

HCID 58444042HCID 58444042, compoundYield 125.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methoxy-tert-butyl-diphenyl-silane (compound 25d, 11 g, 26.6 mmol) in THF (100 mL) was added TBAF solution (1M in THF, 6 mL, 6 mmol) with stirring. After being stirred at room temperature for 4 hours, the reaction solution was washed with saturated NH4Cl solution, dried over Na2SO4, concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether) to afford 5.8 g of [(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol (compound 25e).

Workup

  1. stirringAfter being stirred at room temperature for 4 hours
  2. washthe reaction solution was washed with saturated NH4Cl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-f21baf36705b48b58bc1022f3c4ff533
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

Loading…