Tetrahydrophthalic anhydride, cis- → HCID 10893306, compound

HRID 1871449Notes

Reaction equation

HRID 1871449 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.[Mg].[C:17]1(=[O:27])[O:22][C:20](=[O:21])[C@H:19]2[CH2:23][CH:24]=[CH:25][CH2:26][C@@H:18]12>O1CCCC1>[CH:11]1([O:10][C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=2[O:8][CH3:9])[C:17]([C@H:18]2[CH2:26][CH:25]=[CH:24][CH2:23][C@H:19]2[C:20]([OH:22])=[O:21])=[O:27])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 98495Tetrahydrophthalic anhydride, cis-HCID 5462224MagnesiumHCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

Product 1

HCID 10893306HCID 10893306, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 100 mmol of 1-Bromo-3-cyclopentyloxy-4-methoxybenzene in tetrahydrofuran was added slowly to a mixture of 1.1 equivalent of magnesium. After complete addition, the mixture was refluxed for 5 h and left at room temperature for additional 18 h. The mixture was added slowly to a solution of (cis)-1,2,3,6-tetrahydrophthalic anhydride in tetrahydrofuran at 0° C. After complete addition the mixture was refluxed for 6 h and left at room temperature for addition 18 h after which the reaction was quenched with ammonium chloride and the solvent removed under reduced pressure. The residue was acidified with concentrated hydrochloric acid and the mixture extracted with diethyl ether. The organic layer was dried over magnesium sulfate and evaporated. The residue was dissolved in dichloromethane and the solution filtered over silica. After evaporating this dichloromethane solution, the compound was crystallized from diethyl ether. M.p. 114-115° C.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture was refluxed for 5 h
  3. additionAfter complete addition the mixture
  4. temperaturewas refluxed for 6 h
  5. waitleft at room temperature for addition 18 h after which the reaction
  6. customwas quenched with ammonium chloride
  7. customthe solvent removed under reduced pressure
  8. extractionthe mixture extracted with diethyl ether
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. customevaporated
  11. dissolutionThe residue was dissolved in dichloromethane
  12. filtrationthe solution filtered over silica
  13. customAfter evaporating this dichloromethane solution
  14. customthe compound was crystallized from diethyl ether

Sources & evidence

ORD record
ord-ad1e872fb0b140de84d8fa05849d45d0
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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