2,6-Lutidine → HCID 21472403, compound

HRID 2294964Notes

Reaction equation

HRID 2294964 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[CH2:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1O)[CH:17]=[CH2:18].CC1C=CC=C(C)N=1>ClCCl>[O:8]([C:20]1[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=1[CH2:16][CH:17]=[CH2:18])[S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 2584392-allyl-4-nitrophenol

Product 1

HCID 21472403HCID 21472403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triflic anhydride (1.63 ml) was added dropwise to a mixture of 2-allyl-4-nitrophenol (1.79 g) and 2,6-dimethylpyridine (1.18 g) in dry dichloromethane (15 ml) at -20° C. under an atmosphere of argon. The reaction mixture was allowed to reach ambient temperature over 3 hours. The mixture was partitioned between water and dichloromethane. The organic phase was separated, washed with 1M aqueous sodium hydroxide solution, water, dried (MgSO4) and evaporated to give 2-allyl-4-nitrophenyl triflate (2.71 g) as an oil; microanalysis, found: C, 38.7; H, 2.6; N, 4.2%; C10H8F3NO5S requires: C, 38.6; H, 2.59; N, 4.5%; NMR: 3.7(2H,d), 5.19-5.35(2H,m), 5.97-6.17(1H,m), 7.84(1H,d), 8.36-8.55(2H,m); m/z 311(M).

Workup

  1. customThe mixture was partitioned between water and dichloromethane
  2. customThe organic phase was separated
  3. washwashed with 1M aqueous sodium hydroxide solution, water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ada0f62e4dd9423da364c34733a04024
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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