Dimethyl Sulfate → HCID 12952274, compound

HRID 1577993Notes

Reaction equation

HRID 1577993 reaction equation
O1CCC[CH2:2]1.[Br:6][C:7]1[CH:20]=[C:19]2[C:10]([O:11][C:12]3[CH2:13][CH2:14][CH:15]([OH:22])[CH2:16][C:17]=3[C:18]2=[O:21])=[CH:9][CH:8]=1.[OH-].[Na+].COS(OC)(=O)=O>O.C(Cl)(Cl)Cl>[Br:6][C:7]1[CH:20]=[C:19]2[C:10]([O:11][C:12]3[CH2:13][CH2:14][CH:15]([O:22][CH3:2])[CH2:16][C:17]=3[C:18]2=[O:21])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12952273HCID 12952273, compound

Product 1

HCID 12952274HCID 12952274, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To 100 ml of an anhydrous tetrahydrofuran solution containing 5.9 g of 7-bromo-2-hydroxy-1,2,3,4-tetrahydro-9-xanthone obtained in Example 67 was added 1.1 g of sodium hydroxide (as 55% dispersed in an oil). The mixture was stirred at 50° C. for 1 hour to which was then added dropwise 3.3 g of dimethylsulfate. The resulting mixture was agitated at 60° C. for 1.5 hours. After completion of the reaction, the solvent was removed by distillation to give a residue to which were added chloroform and water. The chloroform phase was collected and washed with water, and then dried with anhydrous sodium sulfate and purified by chromatography on silica gel. The crude crystals thus obtained were recrystallized from benzene/hexane to obtain 3.87 g (yield: 62.6%) of 7-bromo-2-methoxy-1,2,3,4-tetrahydro-9-xanthone as colorless needlelike crystals having a melting point of 139° to 142° C.

Workup

  1. additiondispersed in an oil)
  2. stirringThe resulting mixture was agitated at 60° C. for 1.5 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation
  5. customto give a residue to which
  6. customThe chloroform phase was collected
  7. washwashed with water
  8. dry with materialdried with anhydrous sodium sulfate
  9. custompurified by chromatography on silica gel
  10. customThe crude crystals thus obtained
  11. customwere recrystallized from benzene/hexane

Sources & evidence

ORD record
ord-5d08c020d5ef45c5a947be80dd956a36
Source dataset
uspto-grants-1981_09
Patent number
US04290954

Reaction notes

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