Methyl iodide → 6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one

HRID 2377246Notes

Reaction equation

HRID 2377246 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[CH2:6][CH2:5]2.IC.[C:15](=O)([O-])[O-].[Li+].[Li+]>CN(C)C=O>[OH:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:12])=[CH:3][C:2]=1[O:1][CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11125Lithium CarbonateHCID 115934875,6-Dihydroxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 2331486-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 63 (2.0 g, 12 mmol), iodomethane (1.9 mL, 30 mmol), and lithium carbonate (2.2 g, 30 mmol) in N,N-dimethylformamide (40 mL) was heated to 55° C. for 24 hours. The solution was concentrated under vacuum and was diluted with a 2% solution of hydrochloric acid in water. The precipitate was collected by filtration and was dried under high vacuum to provide the desired product. 1H NMR (500 MHz, CD3OD): δ 2.63 (t, J=6 Hz, 6H), 3.05 (t, J=6 Hz, 6H), 3.98 (s, 3H), 7.05 (s, 2H).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. additionwas diluted with a 2% solution of hydrochloric acid in water
  3. filtrationThe precipitate was collected by filtration
  4. customwas dried under high vacuum

Sources & evidence

ORD record
ord-f393f15970734cbba2ddf2497b0fcb1f
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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