Methyl iodide → HCID 70001255, compound

HRID 380742Notes

Reaction equation

HRID 380742 reaction equation
[C:1]([C:3]1[C:8]2[CH2:9][C:10]3([O:16][C:7]=2[C:6]([O:17][CH3:18])=[CH:5][CH:4]=1)[CH:14]([OH:15])[CH2:13][O:12][CH2:11]3)#[N:2].[H-].[Na+].[CH3:21]I>CN(C)C=O>[C:1]([C:3]1[C:8]2[CH2:9][C:10]3([O:16][C:7]=2[C:6]([O:17][CH3:18])=[CH:5][CH:4]=1)[CH:14]([O:15][CH3:21])[CH2:13][O:12][CH2:11]3)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70002339HCID 70002339, compound

Product 1

HCID 70001255HCID 70001255, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
40 °C

Procedure

2.0 g (8.0 mmol) of 2,3-dihydro-4-cyano-4′-hydroxy-7-methoxybenzofuran-2-spiro-3′-tetrahydrofuran (A11) in 15 ml of dimethylformamide are added dropwise under a nitrogen atmosphere to a solution of 270 mg (8.8 mmol) of 80% strength sodium hydride in 10 ml of dimethylformamide and the mixture is heated at 40° C. for 1 h. 700 μl (10.6 mmol) of methyl iodide, dissolved in 5 ml of dimethylformamide, are then added dropwise at RT. The mixture is stirred at RT for 2 h, concentrated, and the residue is crystallized from 50 ml of water. 1.97 g of the title compound of m.p. 151-156° C. are obtained.

Workup

  1. additionare then added dropwise at RT
  2. concentrationconcentrated
  3. customthe residue is crystallized from 50 ml of water

Sources & evidence

ORD record
ord-99ef51755f644c4199e1e08cfa26f9a4
Source dataset
uspto-grants-2001_10
Patent number
US06303789B1

Reaction notes

Loading…