p-Toluenesulfonic acid → 4-Cyclopropylmethoxy-4-(4-phenylthiazol-2-yl)cyclohexanone

HRID 657518Notes

Reaction equation

HRID 657518 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2([C:16]3[S:17][CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:20]=3)[CH2:15][CH2:14][C:9]3(OCC[O:10]3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH:1]1([CH2:4][O:5][C:6]2([C:16]3[S:17][CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:20]=3)[CH2:15][CH2:14][C:9](=[O:10])[CH2:8][CH2:7]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 594425102-(8-Cyclopropylmethoxy-1,4-dioxaspiro[4.5]dec-8-yl)-4-phenylthiazole

Product 1

HCID 594426254-Cyclopropylmethoxy-4-(4-phenylthiazol-2-yl)cyclohexanoneYield 80.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

8.3 g of 2-(8-cyclopropylmethoxy-1,4-dioxaspiro[4.5]dec-8-yl)-4-phenylthiazole and 5.5 g of p-toluenesulfonic acid were dissolved in 137 ml of acetone and 14 ml of water. The mixture was stirred at room temperature for 4 days, then poured onto 100 ml of a saturated aqueous sodium hydrogencarbonate solution. The acetone was distilled off and the residue extracted three times with 100 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 5.9 g of the title compound were obtained as an amorphous solid.

Workup

  1. distillationThe acetone was distilled off
  2. extractionthe residue extracted three times with 100 ml each of EA
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0c30128bf0f74c999f25ffe83568fa3f
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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