Hexane → HCID 54397250, compound

HRID 1637560Notes

Reaction equation

HRID 1637560 reaction equation
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].[Si:7]([O:14][CH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[C:18]([O:24][CH3:25])[CH:17]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].CCCCCC.C(OCC)(=O)C>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Si:7]([O:14][CH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]([OH:21])[CH2:1][CH:2]([CH3:4])[CH3:3])=[C:18]([O:24][CH3:25])[CH:17]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 19348493HCID 19348493, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 54397250HCID 54397250, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

55 ml (55 mmol) of a 1.0 M solution of isobutyl magnesium bromide in tetrahydrofuran were added to a solution of 23.6 g (73.1 mmol) of tetrabutyl ammonium bromide in 50 ml of tetrahydrofuran, and the resulting mixture was immediately cooled in a dry ice-acetone bath, after which a solution of 10.25 g (36.5 mmol) of 4-t-butyldimethylsilyloxymethyl-2-methoxybenzaldehyde (prepared as described in Preparation 40) in 60 ml of tetrahydrofuran were added dropwise over 30 minutes. After the dropwise addition, the reaction temperature was gradually allowed to return to room temperature, and then the reaction was terminated by adding a saturated aqueous solution of ammonium chloride. The reaction mixture was then extracted with diethyl ether, and the extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 250 g of silica gel using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 3:1 to 2:1 by volume as the eluent, to give 6.81 g (yield 57%) of the title compound as an oily substance.

Workup

  1. temperaturethe resulting mixture was immediately cooled in a dry ice-acetone bath
  2. additionAfter the dropwise addition
  3. customto return to room temperature
  4. customthe reaction was terminated
  5. additionby adding a saturated aqueous solution of ammonium chloride
  6. extractionThe reaction mixture was then extracted with diethyl ether
  7. washthe extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  8. dry with materialafter which it was dried over anhydrous magnesium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. customthe resulting residue was purified by column chromatography through 250 g of silica gel using
  11. washa gradient elution method

Sources & evidence

ORD record
ord-25548c90db83424293e038973dd24aa7
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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