Methyl iodide → HCID 59444118, compound

HRID 1968990Notes

Reaction equation

HRID 1968990 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]=2[N+:19]([O-:21])=[O:20])=[CH:5][CH:4]=1.IC.[CH3:24][Si](C)(C)[N-][Si](C)(C)C.[K+]>C1COCC1.C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:24][O:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[C:12]([N+:19]([O-:21])=[O:20])[CH:13]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 28964239HCID 28964239, compound

Product 1

HCID 59444118HCID 59444118, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [4-({[4-(methyloxy)phenyl]methyl}oxy)-3-nitrophenyl]methanol D117 (2.16 g, 7.47 mmol) in THF (100 mL) was added iodomethane (0.700 mL, 11.20 mmol) followed by the portionwise addition of a 0.5M solution of potassium hexamethyldisilazide (22.40 mL, 11.20 mmol) in toluene. After stirring at rt for 2 hr the mixture was diluted with EtOAc (150 mL) and washed with water (2×50 mL) and brine (2×50 mL). The organic phase was dried (MgSO4) filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 10-40% EtOAc in isohexane to afford the title compound as a pale orange oil which solidified on standing, 1.57 g, 69.3%.

Workup

  1. washwashed with water (2×50 mL) and brine (2×50 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 10-40% EtOAc in isohexane

Sources & evidence

ORD record
ord-b4e573f771be4f4abd437acab334d742
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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