Methanol → Diisopropylether hexane

HRID 1492737Notes

Reaction equation

HRID 1492737 reaction equation
[BH4-].[Na+].[O:3]1[CH2:7][CH2:6]CC1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[CH3:19]O>>[CH3:12][CH2:13][CH2:8][CH2:9][CH2:10][CH3:11].[CH:7]([O:3][CH:8]([CH3:13])[CH3:18])([CH3:6])[CH3:19]

Participants

5

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydride

Product 1

HCID 21881879Diisopropylether hexaneYield 86%

Procedure

19.3 g (511 mmol) of NaBH4 were added to a solution of 78.5 g (341mmol) of the isomer mixture 3/3a in 700 ml of a solvent mixture of tetrahydrofuran/analytical grade methanol (2:1) at room temperature. After the mixture had been stirred at room temperature for 2 hours, 120-130 mL of half-concentrated HC1 were added, and the mixture was extracted with ether. The combined organic phases were dried with Na2SO4. The residue which remained after the solvent had been stripped off was taken up in 500 ml of methylene chloride, and the mixture was heated under reflux with 6.5 g (34mmol) of p-toluenesulfonic acid for 15 minutes. The residue which remained after the solvent had been stripped off was chromatographed on 1.5 kg of silica gel 60.56 g of the isomer mixture 4/4a were able to be isolated in the form of a colorless oil with a mobile phase mixture of hexane/diisopropyl ether 20:1. The overall yield was 86%.

Workup

  1. addition120-130 mL of half-concentrated HC1 were added
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. temperaturethe mixture was heated
  5. customwas chromatographed on 1.5 kg of silica gel 60.56 g of the isomer mixture 4/4a

Sources & evidence

ORD record
ord-97583097abbc4bbb88176019277bcef0
Source dataset
uspto-grants-1994_12
Patent number
US05374752

Reaction notes

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