3-Iodobenzonitrile → HCID 11288409, compound

HRID 1893231Notes

Reaction equation

HRID 1893231 reaction equation
C([Mg]Br)(C)C.I[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11].[O:15]1[C:19]2([CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)[O:18][CH2:17][CH2:16]1>C1COCC1>[OH:25][C:22]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[CH2:23][CH2:24][C:19]2([O:15][CH2:16][CH2:17][O:18]2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 1443413-IodobenzonitrileHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418365HCID 178418365, compound

Product 1

HCID 11288409HCID 11288409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of iso-propyl-magnesium bromide (Aldrich, 2.0 M in THF, 8 mL, 16 mmol) was slowly dropped into a solution of 3-iodo-benzonitrile (Aldrich, 3.25 g, 14.2 mmol) in THF (20 mL) at 0° C. After addition, the reaction was stirred for another 30 min. A solution of 1,4-dioxa-spiro[4.5]decan-8-one (2.22 g, 14.2 mmol) in THF (5 mL) was added to the reaction mixture at 0° C. The reaction was then stirred for additional 2 hours. The reaction was quenched with diluted NH4Cl solution and warmed to room temperature. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow solid, which was purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Workup

  1. additionAfter addition
  2. stirringThe reaction was then stirred for additional 2 hours
  3. customThe reaction was quenched with diluted NH4Cl solution
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a yellow solid, which
  11. customwas purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-344582318a0a4b63b1f42e11a18a30c2
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

Loading…