Tetrabutylammonium Fluoride → HCID 117940148, compound

HRID 627153Notes

Reaction equation

HRID 627153 reaction equation
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][CH:6]1[C:7]([CH2:23][O:24][CH3:25])=[CH:8][C@H:9]2[CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][CH:6]1[C:7]([CH2:23][O:24][CH3:25])=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123597098HCID 123597098, compound

Product 1

HCID 117940148HCID 117940148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Intermediate 122 (1.7 g, 4.61 mmol) in THF (40 mL), TBAF (6.92 mL, 6.92 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. LCMS indicated the disappearance of starting material and formation of the desired product. The mixture was concentrated and purified by silica gel column (40 g, 50-100% Hex/EA) to give the title compound (1.050 g, 90%) as a white solid.

Sources & evidence

ORD record
ord-97d60e9fcea14bc3a0a3b1a4b2e03ad3
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

Loading…