Triethylamine → 3-Methoxynaphthalen-1-yl Trifluoromethanesulfonate

HRID 2090513Notes

Reaction equation

HRID 2090513 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18]1[CH:19]=[C:20](O)[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2.CCN(CC)CC>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[C:18]([O:17][CH3:16])[CH:19]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 109975333-Methoxynaphthalen-1-ol

Product 1

HCID 222228613-Methoxynaphthalen-1-yl TrifluoromethanesulfonateYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (9.35 g, 32.8 mmol) was added dropwise to a solution of 3-methoxy-1-naphthol (5.77 g, 32.8 mmol) and Et3N (10 ml) in dichloromethane (100 ml) at 0° C. with stirring. After 1 h the resulting solution was washed with HCl (50 ml, 1 M) and saturated Na2CO3 (50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using EtOAc (7% in hexanes) to give the title compound (7.45 g, 74%) as a colourless oil.

Workup

  1. washAfter 1 h the resulting solution was washed with HCl (50 ml, 1 M) and saturated Na2CO3 (50 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-ea43e1e7588e44f296cbeae0434ea085
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

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