Methyl iodide → 2-Methylindanone

HRID 735289

Reaction equation

HRID 735289 reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.C1([CH:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[CH2:16]2)C=CC=CC=1.IC>C1COCC1>[CH3:2][CH:16]1[CH2:15][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:24]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 981461-Indanone, 3-phenyl-HCID 2724682Lithium diisopropylamide

Product 1

HCID 2492622-MethylindanoneYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 2 M solution of LDA (21 mL, 1.05 eq, from Aldrich) was added dropwise to 3-phenyl-1-indanone (8.33 g, 40.0 mmol) in THF (300 mL) at −78° C. After 1 h at this temperature, iodomethane (3.00 mL, 1.2 eq) was added. The mixture was stirred at −78° C. for 2 h, at 0° C. for 30 min and quenched with sat NH4Cl (100 mL). After evaporation of THF in vacuo, the aqueous residue was extracted with EtOAc (3×100 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4) and concentrated. Silica gel chromatography (EtOAc-Hex, 5:95 then 7:93 then 10:90) gave the 2-methylindanone (1.93 g, 22%). MS Found: (M+H)+=223.

Workup

  1. customquenched with sat NH4Cl (100 mL)
  2. customAfter evaporation of THF in vacuo
  3. extractionthe aqueous residue was extracted with EtOAc (3×100 mL)
  4. washThe combined extracts were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-327d7b10928b47c39928a5da8eb300f7
Source dataset
uspto-grants-2009_09
Patent number
US07592461B2

Linked notes

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