Tetrabutylammonium Fluoride → HCID 58822601, compound

HRID 459118Notes

Reaction equation

HRID 459118 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([O:7][C@H:8]2[CH2:12][CH2:11][C@@H:10]([O:13][Si](C(C)(C)C)(C)C)[CH2:9]2)=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)C>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([O:7][C@H:8]2[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58822934HCID 58822934, compound

Product 1

HCID 58822601HCID 58822601, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

(1R*,3S*)-[3-(Biphenyl-4-yloxy)-cyclopentyloxy]-tert-butyldimethylsilane (0.25 g, 0.67 mmol) was dissolved in 2 mL of THF and tetrabutylammonium fluoride (0.67 mL, 1M in THF) and stirred at room temperature for 2 hours. The solution was diluted with 15 mL of diethyl ether and washed with 1N HCl (2×15 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 3:1, Rf0.09) to give the product (100%). 1H-NMR (200.15 MHz, CDCl3): δ 7.58–7.26 (m, 7H), 6.95 (d, 2H, J=8.9), 4.92–4.84 (m, 1H), 4.40–4.38 (m, 1H), 2.18–1.92 (m, 7H).

Workup

  1. washwashed with 1N HCl (2×15 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 3:1, Rf0.09)

Sources & evidence

ORD record
ord-8c509bbbae4c44a9aed20965a9896f53
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…