Diethyl Ether → (5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-one

HRID 1180369Notes

Reaction equation

HRID 1180369 reaction equation
[OH:1][C@@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCOCC>C1(C)C=CC=CC=1>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]2[O:4][C:3](=[O:5])[C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[O:1]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 707414-BromobenzaldehydeHCID 83697Leucic acid, L-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 69473106(5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2S)-2-hydroxy-4-methylpentanoic acid (46.4 g, 351 mmol) and 4-bromobenzaldehyde (50 g, 270.2 mmol) were dissolved in 400 ml toluene and pyridinium 4-methylbenzenesulfonate (340 mg, 1.35 mmol) was added. The mixture was refluxed in a Dean-Stark for 24 hours. The mixture was cooled, poured into 500 ml NaHCO3(sat) and 500 ether, the phases were separated and the organic phase washed with 500 ml NaHCO3(sat.) and brine. The organic phase was dried with Na2SO4 and the solvent striped. 400 ml Hexane was added to the resulting solid and the mixture was stirred 1 hour in salt ice bath. The solution was filtered thru Celite, and the solvent removed. (5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-one (3:2 mixture of cis/trans) was obtained.

Workup

  1. temperatureThe mixture was refluxed in a Dean-Stark for 24 hours
  2. temperatureThe mixture was cooled
  3. customthe phases were separated
  4. washthe organic phase washed with 500 ml NaHCO3(sat.) and brine
  5. dry with materialThe organic phase was dried with Na2SO4
  6. addition400 ml Hexane was added to the resulting solid
  7. filtrationThe solution was filtered thru Celite
  8. customthe solvent removed

Sources & evidence

ORD record
ord-1119f1a6e20e41cda8f152f3a4107caa
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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