Methyl iodide → HCID 117667862, compound

HRID 514205Notes

Reaction equation

HRID 514205 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:17](=[O:18])[CH:16]3[CH:11]([CH:12]4[O:19][CH:15]3[CH2:14][CH2:13]4)[C:10]2=[O:20])=[C:4]([CH3:21])[CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:17](=[O:18])[CH:16]3[CH:11]([C:10]=2[O:20][CH3:22])[CH:12]2[O:19][CH:15]3[CH2:14][CH2:13]2)=[C:4]([CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75274566HCID 75274566, compound

Product 1

HCID 117667862HCID 117667862, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 4-(4-Bromo-2,6-dimethylphenyl)-10-oxatricyclo[5.2.1.0*2,6*]decane-3,5-dione (1.0 g, 2.86 mmol) (reported in WO 2009019005) in acetone (50 ml) is added potassium carbonate (0.59 g, 4.3 mmol) followed by iodomethane (2.0 g, 0.89 ml, 14 mmol). The mixture is stirred at room temperature for 18 hours then acetone is removed in vacuo and the residue is partitioned between water and ethyl acetate. The crude product is extracted with ethyl acetate and the combined organic fractions are washed with distilled water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford (1RS,2SR,6RS,7SR)-4-(4-bromo-2,6-dimethylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one.

Workup

  1. customacetone is removed in vacuo
  2. customthe residue is partitioned between water and ethyl acetate
  3. extractionThe crude product is extracted with ethyl acetate
  4. washthe combined organic fractions are washed with distilled water
  5. dry with materialbrine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0169d69477840e6b76ab2d41d6136b2
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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