p-Toluenesulfonic acid → HCID 68716235, compound

HRID 29326Notes

Reaction equation

HRID 29326 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([OH:19])[CH2:17][OH:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[C:20]1(C)[CH:25]=CC(S(O)(=O)=O)=C[CH:21]=1.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]3[CH2:17][O:18][C:20]([CH3:25])([CH3:21])[O:19]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 687114494-(1,2-Dihydroxyethyl)-3-methylbenzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 68716235HCID 68716235, compoundYield 973.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 0.150 g (0.568 mmol) of 4-(1,2-dihydroxyethyl)-3-methylbenzofuran-2-carboxylic acid ethyl ester dissolved in 5 mL of acetone was added 0.010 g of p-toluenesulfonic acid and the reaction was stirred at room temperature overnight. Saturated sodium bicarbonate was added and the acetone was removed in vacuo. The residue was extracted with ether, the organics were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:5) to provide 0.172 g of 4-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylbenzofuran-2-carboxylic acid ethyl ester.

Workup

  1. customthe acetone was removed in vacuo
  2. extractionThe residue was extracted with ether
  3. dry with materialthe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:5)

Sources & evidence

ORD record
ord-241072a00e0d4116a61938df6344e67c
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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