Triethylamine → 5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

HRID 1446601Notes

Reaction equation

HRID 1446601 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].O[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[CH2:22][CH2:21][CH2:20]2.C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:26]=[CH:25][C:24]2[C:23](=[O:27])[CH2:22][CH2:21][CH2:20][C:19]=2[CH:18]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (2.51 mL) was added to a solution of 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (2.00 g) and triethylamine (4.11 mL) in dichloromethane (20 mL) at −20° C., and the reaction solution was stirred at that temperature for 20 minutes. After confirming that the raw materials disappeared, the reaction solution was concentrated under reduced pressure, and water and chloroform were added to the residue and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent:heptane-ethyl acetate system) to obtain 3.30 g of the title compound. Properties data of the compound are as follows.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure, and water and chloroform
  2. additionwere added to the residue
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (elution solvent:heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-b4939dd2005040e99bac60975397f240
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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