Methyl iodide → HCID 54416601, compound

HRID 1417507Notes

Reaction equation

HRID 1417507 reaction equation
[C:1](=O)([O-])[O-].CI.[CH2:7]([N:14]1[C:26]2[C:25]([OH:27])=[C:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:23]=[C:22]([CH3:33])[C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:7]([N:14]1[C:26]2[C:25]([O:27][CH3:1])=[C:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:23]=[C:22]([CH3:33])[C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 53695325HCID 53695325, compound

Product 1

HCID 54416601HCID 54416601, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

120 mg of anhydrous pottasium carbonate and 0.14 ml of methyl iodide were added to 4 ml of a solution of 80 mg of methyl (9-benzyl-1-hydroxy-4-methylcarbazol-2-yl)acetate, as obtained in Example 219, in dimethyl formamide, at room temperature, and the reaction mixture was stirred for 1 hour. After this time, the reaction mixture was diluted with an excess of ethyl acetate, and then washed with a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over anhydrous sodium sulfate and then the solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 15-20% v/v solution of ethyl acetate in hexane) to yield 84 mg of the title compound as a solid.

Workup

  1. washwashed with a saturated aqueous solution of sodium chloride
  2. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3e2aecfe4417439486974c5cc2f4add9
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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