Methyl iodide → HCID 18690791, compound

HRID 1871247Notes

Reaction equation

HRID 1871247 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([CH:20]=[O:21])[CH2:14]2)([CH3:10])([CH3:9])[CH3:8].CI>CCOCC>[C:7]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15]([CH3:1])([CH:20]=[O:21])[CH2:14]2)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 18350561HCID 18350561, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18690791HCID 18690791, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of potassium tert-butoxide (Fluka, 0.45 g, 4 mmole) and of 5-tert-butyl-2-indancarbaldehyde (ex. 4; 0.71 g, 3.5 mmole), there was added at room temperature and under N2, methyl iodide (0.56 g, 4 mmole) and reaction was allowed at room temperature, under stirring. The mixture was taken in ether and washed with NH4Cl and brine, dried over Na2SO4 and concentrated (0,9 g). Chromatography on SiO2 (30 g), with toluene as eluting agent, provided 50 mg (purity>99%, yield 7%) of the desired aldehyde.

Workup

  1. customwas allowed at room temperature
  2. washwashed with NH4Cl and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated (0,9 g)
  5. washChromatography on SiO2 (30 g), with toluene as eluting agent

Sources & evidence

ORD record
ord-acdd697456e843668ae36f2080b09fe7
Source dataset
uspto-grants-2000_08
Patent number
US06103688

Reaction notes

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