2,6-Lutidine → 2-Trifluoromethylsulphonyloxy-5-(2-methoxyethoxy)benzaldehyde

HRID 580976Notes

Reaction equation

HRID 580976 reaction equation
[F:1][C:2]([S:5]([O:8]S(C(F)(F)F)(=O)=O)(=[O:7])=[O:6])([F:4])[F:3].O[C:17]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:21][C:18]=1[CH:19]=[O:20].CC1C=CC=C(C)N=1>ClCCl>[F:1][C:2]([F:4])([F:3])[S:5]([O:8][C:17]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:21][C:18]=1[CH:19]=[O:20])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 537546562-Hydroxy-5-(2-methoxyethoxy)benzaldehyde

Product 1

HCID 542460612-Trifluoromethylsulphonyloxy-5-(2-methoxyethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethyl sulphonic anhydride (3.88 ml) was added dropwise over a period of 10 minutes to a stirred solution of 2-hydroxy-5-(2-methoxyethoxy)benzaldehyde (4.11 g) and 2,6-dimethylpyridine (2.67 ml) in dichloromethane (20 ml) at 0° C. under an atmosphere of argon. After stirring at room temperature for 16 hours, the mixture was added to ice (100 g). The organic phase was separated, washed with 5% aqueous sodium carbonate solution (2×10 ml), dried (MgSO4) and evaporated to give an oil which was purified by flash column chromatography on silica gel using dichloromethane as eluent to give 2-trifluoromethylsulphonyloxy-5-(2-methoxyethoxy)benzaldehyde (2.2 g) as an oil; NMR(CDCl3): 3.45(3H,s), 3.78(2H,m), 4.19(2H,m), 7.3(2H,m), 7.48(1H,d) and 10.23(1H,d); m/z 329(M+H).

Workup

  1. customThe organic phase was separated
  2. washwashed with 5% aqueous sodium carbonate solution (2×10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil which
  6. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ba5da0025f374174bf8b740e645dc833
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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