Methyl iodide → HCID 117759708, compound

HRID 1049580Notes

Reaction equation

HRID 1049580 reaction equation
[C:1](=[O:29])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23]#[C:24][C:25]([OH:28])([CH3:27])[CH3:26])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].I[CH3:31]>C1(C)C=CC=CC=1.[Ag-]=O.[Ag+]>[C:1](=[O:29])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23]#[C:24][C:25]([O:28][CH3:31])([CH3:27])[CH3:26])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 117759720HCID 117759720, compound

Product 1

HCID 117759708HCID 117759708, compound

Reagents, catalysts & solvents 3

HCID 104755Silver cationCatalystHCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 2′-fluoro-2-(3-hydroxy-3-methylbut-1-yn-1-yl)-5′-methoxybiphenyl-4-yl carbonate (314 mg) and iodomethane (0.50 mL) in toluene (5 mL) was added silver(I) oxide (365 mg). After stirring at 40° C. for 20 hr, silver(I) (365 mg) was added to the reaction mixture. The mixture was stirred at 40° C. for 70 hr. The reaction mixture was filtered, the solvent of the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (244 mg) as a colorless oil.

Workup

  1. stirringThe mixture was stirred at 40° C. for 70 hr
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent of the filtrate was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9a9f34fbdcc3416993a4bf27548709fd
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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