Water → HCID 59186632, compound

HRID 731548Notes

Reaction equation

HRID 731548 reaction equation
[CH3:1][O:2][C:3]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:1][O:2][C:3]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:12][CH2:11][C:6](=[O:7])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 59186664HCID 59186664, compound

Product 1

HCID 59186632HCID 59186632, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of EXAMPLE 15B (0.51 g, 1.80 mmol) in acetone (10 mL) was treated with water (5 mL) and p-toluenesulfonic acid monohydrate (0.20 g), heated to reflux, stirred overnight, and concentrated to remove the acetone. The remaining aqueous solution was extracted with ethyl acetate (3×100 mL) and the combined extracts were washed sequentially with 1N NaOH, water, and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product (0.42 g, 100%). MS (ESI) m/e 233 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customto remove the acetone
  5. extractionThe remaining aqueous solution was extracted with ethyl acetate (3×100 mL)
  6. washthe combined extracts were washed sequentially with 1N NaOH, water, and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2d2b0ee01cb54783825a25444ad4c694
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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