6-Bromo-1,4-benzodioxane → HCID 20089281, compound

HRID 274894Notes

Reaction equation

HRID 274894 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[Mg].Br[C:14]1[CH:23]=[CH:22][C:17]2[O:18]CCO[C:16]=2[CH:15]=1>C1COCC1>[O:11]1[C:4]2[CH:9]=[CH:8][C:7]([C:17]3([OH:18])[CH2:22][CH2:23][CH2:14][CH2:15][CH2:16]3)=[CH:6][C:5]=2[O:3][CH2:2][CH2:1]1

Participants

5

Reactant 3

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

Product 1

HCID 20089281HCID 20089281, 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 1 N 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 1 N 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-ce3b8fb466ab4136ae9961317d1f93e3
Source dataset
uspto-grants-1995_02
Patent number
US05391570

Reaction notes

Loading…