Methyl iodide → HCID 117664789, compound

HRID 2199490Notes

Reaction equation

HRID 2199490 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:27]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:27][O:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 117664395HCID 117664395, compound

Product 1

HCID 117664789HCID 117664789, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve compound 8 (1.2 g, 3.4 mmol) in DMF (20 ml), add anhydrous K2CO3 (0.7 g, 5.1 mmol), MeI (0.96 g, 6.8 mmol), react at 60° C. for 2h. After completion of the reaction, cool the mixture, filter and evaporate the DMF from filtrate under reduced pressure, feed the redissolved residue solution to a silica gel column, evaporate the solvent in the eluent to obtain a colorless oil (1.12 g, 90%). 1H NMR (400 MHz, DMSO-d6): 1.62 (s, 3H), 1.71 (s, 3H), 3.23 (d, J=6.4 Hz, 2H), 3.68 (s, 3H), 3.86 (s, 3H), 3.90 (s, 3H), 5.10 (t, J=6.4 Hz, 1H), 6.98 (d, J=16.0 Hz, 1H), 7.18 (s, 1H), 7.28 (t, J=7.2 Hz, 1H), 7.30 (d, J=16.0 Hz, 1H), 7.38 (t, J=7.2 Hz, 2H), 7.53 (d, J=7.2 Hz, 2H).

Workup

  1. customreact at 60° C. for 2h
  2. customAfter completion of the reaction
  3. temperaturecool the mixture
  4. filtrationfilter
  5. customevaporate the DMF from filtrate under reduced pressure
  6. customevaporate the solvent in the eluent

Sources & evidence

ORD record
ord-0583146758d648379cbf46f4a220ed9e
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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