5-Hydroxy-2-pentanone → 5-(Benzyloxy)pentan-2-one

HRID 1919766Notes

Reaction equation

HRID 1919766 reaction equation
Cl[C:2](Cl)(Cl)[C:3](=N)[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.OCC[CH2:18][C:19](=[O:21])[CH3:20].FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:5]([O:4][CH2:3][CH2:2][CH2:18][C:19](=[O:21])[CH3:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 140665-Hydroxy-2-pentanoneHCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 516892Sodium Bicarbonate

Product 1

HCID 2812685-(Benzyloxy)pentan-2-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl trichloroacetimidate (1.85 g) was added to a mixed solution of 5-hydroxy-2-pentanone (500 mg, 4.89 mmol) in dichloromethane (20 mL) in an argon atmosphere at room temperature, and then trifluoromethanesulfonic acid (87 μL) was added in an ice bath. The mixture was returned to room temperature and stirred overnight. After completion of the reaction, a saturated sodium bicarbonate solution was added to the reaction solution in an ace bath, and the pH was adjusted to 8. After extraction with chloroform-water, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 610 mg of the title compound (yield: 65%) as a pale yellow oil.

Workup

  1. customwas returned to room temperature
  2. customAfter completion of the reaction
  3. extractionAfter extraction with chloroform-water
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-45f2d1c6054c457da73601f9485ec5b1
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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