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

HRID 1439882Notes

Reaction equation

HRID 1439882 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 purtification.

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%)

Sources & evidence

ORD record
ord-90d3c5941f6f408fb244b953200c8e87
Source dataset
uspto-grants-1996_03
Patent number
US05496847

Reaction notes

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