Methyl iodide → 4-methoxy-2,3-dihydro-1H-inden-1-one

HRID 1369006Notes

Reaction equation

HRID 1369006 reaction equation
[C:1]([O-])([O-])=O.[Cs+].[Cs+].CI.[OH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH2:13][C:14]2=[O:19]>C1COCC1>[CH3:1][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH2:13][C:14]2=[O:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cs2CO3 (7 g; 21.5 mmol) followed by CH3I (10 g; 70 mmol) was added to a solution of 4-hydroxy-1-indanone (5.0 g; 34 mmol) in THF (30 mL) and the mixture was stirred at RT for 60 h. The reaction mixture was filtered and concentrated, and the crude product was purified using flash chromatography (SiO2; methylene chloride) to yield 3.1 g (56%) of the sub-title substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe crude product was purified
  4. customto yield 3.1 g (56%) of the sub-title substance

Sources & evidence

ORD record
ord-44a0ad830bf349e290bde71a349175db
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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