Hydrochloric Acid → 2-[4-(2-Methylbutyryl)benzyl]anisole

HRID 895649Notes

Reaction equation

HRID 895649 reaction equation
C(N(CC)[C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:8][CH:7]=1)=[O:5])C.[CH:23]([Li])([CH2:25][CH3:26])[CH3:24].Cl>C1(C)C=CC=CC=1.CCCCCC.C1CCCCC1>[CH3:24][CH:23]([CH2:25][CH3:26])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:19][CH:20]=1)=[O:5]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 223806822-(4-Diethylcarbamoylbenzyl)anisoleHCID 178418400CID 53628100

Product 1

HCID 223805962-[4-(2-Methylbutyryl)benzyl]anisoleYield 61%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

The 2-(4-diethylcarbamoylbenzyl)anisole (100 mg) obtained in the process of Reference Example 1(d) was dissolved in toluene (2 ml), added with a solution of sec-butyl lithium in n-hexane and cyclohexane (1.0 M, 0.47 ml) at 0° C. under argon atmosphere and stirred at room temperature for 1 hour. After the reaction mixture was slowly poured into 1 N aqueous hydrochloric acid (5 ml) with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with ether (10 ml). The organic layer was washed with saline and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1) to obtain 58.3 mg of the title compound. Yield: 61%.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with ether (10 ml)
  5. washThe organic layer was washed with saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-74a497591a954d9d989c51a3d92f9b12
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

Loading…