Tetrabutylammonium Fluoride → 113274-28-5

5c. A 1.0M solution (100 mL) of tetra-n-butylammonium fluoride in tetrahydrofuran was added dropwise to a stirred solution of 1-(2-(tert-butyldimethylsiloxy)ethyl)-3-methyl-3-(N-methylcarbamoyl)triazene in tetra-hydrofuran at -10° C. over 1 h. The volume of the solution was then reduced 50% with a rotary evaporator at 25° C. and the resultant solution was chromatographed on a column of 250 g of Silica Gel 60 (EM, neutral, 70-230 mesh) packed in ether. The column was eluted with 5 L of ether. The last 3 L of eluent were concentrated on a rotary evaporator and the residue (6.7 g) recrystallized from methylene chloride-ether to give 4.24 g of 1-(2-hydroxyethyl)-3-methyl-3-(N-methylcarbamoyl)triazene, 5c, (0.0265 mol, 27.8%): mp 72°-74° C.; IR (CH2Cl2) 3600, 3450, 2955, 1690, 1510, 1190, 1050 cm10-1 ; UV (CH3CN) λ max 245 (log ε 4.04); 1H NMR (CDCl3, Me4Si) δ 1.78 (1H ,t,J=6 Hz), 2.94 (3H,d,J=5 Hz), 3.26 (3H,s), 3.97 (2H,t,J=5 Hz), 4.02 (2H,m-A2B2X), 6.34 (1H,b); proton decoupled 13C NMR (CDCl3, Me4Si) δ 26.86, 27.60, 60.72, 155.54; exact mass calcd m/z for C5H12N4 o2 160.0960, found 160.0967 (by EI).

1. customwith a rotary evaporator at 25° C.
2. customthe resultant solution was chromatographed on a column of 250 g of Silica Gel 60 (EM, neutral, 70-230 mesh)
3. washThe column was eluted with 5 L of ether
4. concentrationThe last 3 L of eluent were concentrated on a rotary evaporator
5. customthe residue (6.7 g) recrystallized from methylene chloride-ether

ORD record

ord-f44a6022e3c84e28bc073912c1f2f3ca

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04923970