Tetrabutylammonium Fluoride → HCID 19370230, compound

HRID 129869Notes

Reaction equation

HRID 129869 reaction equation
[C:1]1([N:7]2[CH2:13][CH2:12][C:11]([CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:10][CH:9]([CH2:34][C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])[C:8]2=[O:45])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]1([N:7]2[CH2:13][CH2:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]([CH2:34][C:35]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:36])[C:8]2=[O:45])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10348881HCID 10348881, compound

Product 1

HCID 19370230HCID 19370230, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound (11) (388 mg, 0.628 mmol) was dissolved in tetrahydrofuran (3 mL) and treated at room temperature with 1.26 mL of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran for 4 h. The reaction mixture was then evaporated at reduced pressure and the residue purified by flash chromatography (silica gel, 2.5×20 cm, 65% ethyl acetate/hexane) to yield the title compound (12) (158 mg, 66%). Compound (12): 1H NMR (CDCl3) δ 1.77-3.27 (7H, m), 3.40-3.73 (1H, m), 3.67 (2H, t, J=6 Hz), 4.20-4.77 (2H, m), 5.07-5.40 (3H, m), 7.07-7.58 (10H, m); TLC Rf 0.33 (silica gel, 1:3 hexane:ethyl acetate).

Workup

  1. customThe reaction mixture was then evaporated at reduced pressure
  2. customthe residue purified by flash chromatography (silica gel, 2.5×20 cm, 65% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-95e09739f563435c94fd6ac676779bfc
Source dataset
uspto-grants-1995_11
Patent number
US05470849

Reaction notes

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