Methanol → HCID 12178333, compound

HRID 585782Notes

Reaction equation

HRID 585782 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:35])[C:12]2[C:13](=[O:34])[C:14]3[C:19]([O:20][C:21]=2[C:22]=1[CH2:23][CH:24]=[CH2:25])=[C:18]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:17]=[CH:16][CH:15]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:38]I.CO>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:35][CH3:38])[C:12]2[C:13](=[O:34])[C:14]3[C:19]([O:20][C:21]=2[C:22]=1[CH2:23][CH:24]=[CH2:25])=[C:18]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH:17]=[CH:16][CH:15]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 11190472HCID 11190472, compound

Product 1

HCID 12178333HCID 12178333, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of xanthone 6 (63 g, 135 mmol) in dry DMF (300 mL) was added sodium hydride (9 g 60% in oil, 225 mmol) portionwise at room temperature. Methyl Iodide (180 g, 1.28 mol) was added and the mixture was heated to 50° C. for 90 minutes. The reaction was then chilled with an ice bath and methanol was added dropwise (20 mL) until the remaining sodium hydride was consumed. The reaction mixture was diluted with ethyl acetate (1.2L) and washed with brine (3×500 mL), dried over magnesium sulfate, filtered over a pad of silica gel (60×100 mm) and the solvent was removed in vacuo to afford the xanthone 7 as a solid (55 g, 115 mmol, 85%).

Workup

  1. temperatureThe reaction was then chilled with an ice bath
  2. customwas consumed
  3. additionThe reaction mixture was diluted with ethyl acetate (1.2L)
  4. washwashed with brine (3×500 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered over a pad of silica gel (60×100 mm)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ba21063afca84dbc848f5b6053d84b40
Source dataset
uspto-grants-2005_08
Patent number
US06933396B2

Reaction notes

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