6-Bromo-1,4-benzodioxane → HCID 22924041, compound

HRID 2257970Notes

Reaction equation

HRID 2257970 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3]C1.[Mg].Br[C:14]1[CH:23]=[CH:22][C:17]2[O:18][CH2:19][CH2:20][O:21][C:16]=2[CH:15]=1>C1COCC1>[O:18]1[C:17]2[CH:22]=[CH:23][C:14]([C:7]3([OH:10])[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]3)=[CH:15][C:16]=2[O:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 1041416-Bromo-1,4-benzodioxaneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

Product 1

HCID 22924041HCID 22924041, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,4-cyclohexanedione monoethylene ketal (7.8 g, 50 mmole) in 50 ml dry THF was added to a of the Grignard reagent prepared from magnesium metal (1.34 g, 55 mmole) and 6-bromo-1,4-benzodioxane (10.75 g, 50 mmole). The mixture was stirred for 16 hr, quenched with saturated NH4Cl and extracted with ether. The ether extracts were dried with Na2SO4 and the solvent removed in vacuo. Acetone (75 ml) and 1N HCl (75 ml) were added and the solution was stirred 18 hr to give a tan precipitate which was filtered and air dried (6.38 g, 59.1%). This material was used without further purification.

Workup

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ether
  3. dry with materialThe ether extracts were dried with Na2SO4
  4. customthe solvent removed in vacuo
  5. additionAcetone (75 ml) and 1N HCl (75 ml) were added
  6. stirringthe solution was stirred 18 hr
  7. customto give a tan precipitate which
  8. filtrationwas filtered
  9. customair dried (6.38 g, 59.1%)
  10. customThis material was used without further purification

Sources & evidence

ORD record
ord-0d050252605946d6a6e6670939b82801
Source dataset
uspto-grants-1997_08
Patent number
US05658941

Reaction notes

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