Methyl iodide → HCID 70091066, compound

HRID 260129Notes

Reaction equation

HRID 260129 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[C:16]2[CH2:24][C:23]3[C:18](=[CH:19][C:20]([C:25]([OH:27])=[O:26])=[CH:21][CH:22]=3)[C:17]2=[O:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]([O-])([O-])=O.[Cs+].[Cs+].CI>CO.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[C:16]2[CH2:24][C:23]3[C:18](=[CH:19][C:20]([C:25]([O:27][CH3:29])=[O:26])=[CH:21][CH:22]=3)[C:17]2=[O:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 53740709HCID 53740709, compound

Product 1

HCID 70091066HCID 70091066, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 2-1 (4.5 g, 11.7 mmol) in CH3OH (120 mL) was treated with Cs2CO3 (1.9 g, 5.85 mmol) to give a homogenous solution. The solvent was removed in vacuo and the resulting solid was dissolved in DMF (120 mL) and treated with methyliodide (0.72 mL, 11.7 mmol) at room temperature for 18 h. The solution was diluted with EtOAc and washed with H2O, sat. NaHCO3 and brine. The organic layer was dried (MgSO4), filtered, concentrated, and chromatographed (30% EtOAc/Hexanes) to give 2-2 as a white solid. Rf (30% EtOAc/Hexanes) 0.15 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 8.28 (d, 1H), 7.58 (d, 1H), 6.94 (m, 1H), 4.1 (bd, 2H), 3.93 (s, 3H), 3.7 (s, 2H), 2.7 (bt, 2H), 2.28 (t, 2H), 1.7 (m, 3H), 1.45 (m, 9H), 1.2 (m, 2H).

Workup

  1. customto give a homogenous solution
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting solid was dissolved in DMF (120 mL)
  4. washwashed with H2O, sat. NaHCO3 and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-53c3e8c777b244aaa1db71eae5d37177
Source dataset
uspto-grants-1996_06
Patent number
US05525617

Reaction notes

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