Toluene → Ethyl 2-(trifluoromethyl)furan-3-carboxylate

HRID 1654116Notes

Reaction equation

HRID 1654116 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[O:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].C1(C)C(S(O)(=O)=[O:19])=CC=CC=1.[C:23]1([CH3:29])C=CC=CC=1>>[F:11][C:2]([F:1])([F:10])[C:3]1[O:4][CH:5]=[CH:6][C:7]=1[C:8]([O:19][CH2:23][CH3:29])=[O:9]

Participants

4

Reactant 3

HCID 1140TolueneHCID 69252-Methylbenzenesulfonic acidHCID 17953606(2-Trifluoromethyl-furan-3-yl)-methanol

Product 1

HCID 4737733Ethyl 2-(trifluoromethyl)furan-3-carboxylate

Procedure

43.g of the product of Stage A were refluxed for 2 and a half hours in 250 ml of toluene and 3.1 g of toluenesulfonic acid and the reaction mixture was allowed to cool and was chromatographed on silica (eluent: 9/1 hexane/ethyl acetate) to obtain after evaporation of the solvent at 40° C. under 80 mm of Hg, 20 g of the expected product.

Workup

  1. temperatureto cool
  2. customwas chromatographed on silica (eluent: 9/1 hexane/ethyl acetate)
  3. customto obtain
  4. customafter evaporation of the solvent at 40° C. under 80 mm of Hg, 20 g of the expected product

Sources & evidence

ORD record
ord-11b84bce1d4444bb92259494d505390c
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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