2-Methoxyethanol → HCID 22273536, compound

HRID 1064331Notes

Reaction equation

HRID 1064331 reaction equation
O([CH2:9][CH2:10][O:11][CH3:12])S(C(F)(F)F)(=O)=O.COCCO.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:40]2[CH:44]=[C:43]([C:45](=[O:47])[CH3:46])[N:42]=[C:41]2[CH3:48])C=CC=CC=1>C(Cl)Cl>[CH3:12][O:11][CH2:10][CH2:9][N:42]1[C:43]([C:45](=[O:47])[CH3:46])=[CH:44][N:40]=[C:41]1[CH3:48]

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 22273469HCID 22273469, compoundHCID 222734932-Methoxyethyl trifluoromethanesulfonate

Product 1

HCID 22273536HCID 22273536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methoxyethyl triflate (prepared on a 6 mmole scale from 2-methoxyethanol and trifluoromethanesulphonic anhydride by the method published in Synthesis 1982 85) in DCM (20 ml) was added dropwise to a solution of 1-(triphenylmethyl)-2-methyl-4-acetylimidazole (Method 34; 1.5 g, 4 mmol) in DCM (5 ml) and the mixture was stirred for 40 hours at ambient temperature. The volatiles were removed by evaporation to give a solid (2.4 g) which was purified by flash chromatography on silica gel eluting with DCM/MeOH (100:0 increasing in polarity to 95:5) to yield the title compound (660 mg, 88%) as a solid NMR (CDCl3) 1.31 (s, 3H), 1.49 (s, 3H), 2.02 (s, 3H), 2.43 (m, 2H), 3.31 (m, 2H), 6.87 (s, 1H); m/z 183.

Workup

  1. customThe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-234fd86570c4499c9b313709d13e6df4
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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