1,2-Dimethoxyethane → HCID 59192511, compound

HRID 2384002Notes

Reaction equation

HRID 2384002 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:8]=[C:7]([O:20]S(C(F)(F)F)(=O)=O)[C:6]=2[CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC>[Cl-].[NH4+]>[OH:20][C:7]1[C:6]2[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:11]=2[CH:10]=[C:9]([O:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:15])=[O:14])[CH:8]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 59192495HCID 59192495, compound

Product 1

HCID 59192511HCID 59192511, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of trifluoro-methanesulfonic acid 8-oxo-4-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-2-yl ester (XXVII, 542 mg, 1.23 mmol) and cesium carbonate (599 mg, 1.84 mmol) was added dimethoxyethane (11 mL) at room temperature. The resulting brown suspension was then heated at 80° C. and stirred for 3 h. The reaction mixture was cooled to room temperature and diluted with saturated ammonium chloride solution (50 mL), and then extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The crude product was dissolved in dichloromethane (15 mL) and diluted with hexanes (100 mL), then heated to remove the dichloromethane. The cloudy solution was then stored in the refrigerator for 15 h. The resulting solids were collected by filtration and washed with hexanes. After drying in the air, trifluoro-methanesulfonic acid 4-hydroxy-8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (182 mg, 51%) was obtained as a dark brown solid: ES(−)-HRMS m/e calcd. for C11H9F3O5S (M−H)− 309.0050, obsd. 309.0049.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were washed with brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. dissolutionThe crude product was dissolved in dichloromethane (15 mL)
  8. additiondiluted with hexanes (100 mL)
  9. temperatureheated
  10. customto remove the dichloromethane
  11. waitThe cloudy solution was then stored in the refrigerator for 15 h
  12. filtrationThe resulting solids were collected by filtration
  13. washwashed with hexanes
  14. customAfter drying in the air

Sources & evidence

ORD record
ord-b703fb35b48743c993b98eea0a40c12a
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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