Methyl iodide → HCID 58424200, compound

HRID 2096650Notes

Reaction equation

HRID 2096650 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[O:14][C:7]1([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:18].[O-]S([O-])(=O)=O.[Ca+2].[CH3:25]I>>[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[O:14][C:7]1([CH2:8][CH2:9][CH:10]([O:13][CH3:25])[CH2:11][CH2:12]1)[CH2:6][C:5]2=[O:18]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24497Calcium SulfateHCID 58423839HCID 58423839, compound

Product 1

HCID 58424200HCID 58424200, compoundYield 100%

Procedure

In a 20 mL vial was placed 6-bromo-4′-hydroxyspiro[chroman-2,1′-cyclohexan]-4-one (46 mg, 0.148 mmol) and it was azeotroped with acetonitrile (3 mL) The solid was dissolved in acetonitrile (1 mL) To this heterogenous solution was added Ag2O (103 mg, 0.444 mmol) followed by freshly grounded Drierite (160 mg). Then MeI (185 μL, 2.97 mmol) was added, the vial was capped and the reaction was allowed to stir at room temperature. After 2 days stirring the alcohol was totally consumed. The reaction mixture was filtered through a plug of Celite and the cake was rinsed with ethyl acetate three times (2 mL/each). The filtrate was concentrated yielding crude 6-bromo-4′-methoxyspiro[chroman-2,1′-cyclohexan]-4-one (48 mg, 0.148 mmol, 100% yield) which by 1H NMR looked >90% pure.

Workup

  1. customwas azeotroped with acetonitrile (3 mL) The solid
  2. dissolutionwas dissolved in acetonitrile (1 mL) To this heterogenous solution
  3. customthe vial was capped
  4. customwas totally consumed
  5. filtrationThe reaction mixture was filtered through a plug of Celite
  6. washthe cake was rinsed with ethyl acetate three times (2 mL/each)
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c70b26543aee41e596aa7a31583e3355
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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