Methyl iodide → HCID 69018133, compound

HRID 133849Notes

Reaction equation

HRID 133849 reaction equation
[OH:1][CH:2]([C:7]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[C:3]([O:5][CH3:6])=[O:4].I[CH3:17]>C(OCC)C.[Ag-]=O>[CH3:17][O:1][CH:2]([C:7]([CH3:15])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 12656922HCID 12656922, compound

Product 1

HCID 69018133HCID 69018133, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 2-hydroxy-3-methyl-3-phenylbutanoate (0.50 g, 2.4 mmol, from Reference Example 37) in diethyl ether (11 mL) is added silver (I) oxide (4.3 g) and iodomethane (8.7 mL). The reaction mixture is stirred in a 40° C. oil bath under nitrogen atmosphere for 26 hours. The reaction mixture is combined with that from a previous run conducted under the same conditions and filtered through a plug of diatomaceous earth. The filtrate is concentrated under reduced pressure and then purified by flash chromatograhy (silica gel, hexanes/ethyl acetate) to furnish 0.52 g of a clear, colorless liquid (68% combined yield). MS (ES+): (M+H)=222.9

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. custompurified by flash chromatograhy (silica gel, hexanes/ethyl acetate)
  4. customto furnish 0.52 g of a clear,
  5. customcolorless liquid (68% combined yield)

Sources & evidence

ORD record
ord-1108b76155b246319deeada04611e0a7
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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