Pentane → 1,3-Dioxolan-4-one, 2-(1,1-dimethylethyl)-5-phenyl-, (2R,5R)-

HRID 453329Notes

Reaction equation

HRID 453329 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].CCCCC.[CH3:17][C:18]([CH:21]=O)([CH3:20])[CH3:19].C([O-])(O)=O.[Na+]>FC(F)(F)S(O)(=O)=O>[C:18]([C@H:21]1[O:10][C:1](=[O:11])[C@@H:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[O:3]1)([CH3:20])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 8003PentaneHCID 11914(-)-Mandelic acidHCID 12417PivalaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 110094971,3-Dioxolan-4-one, 2-(1,1-dimethylethyl)-5-phenyl-, (2R,5R)-Yield 88%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidCatalyst

Conditions

Temperature
36 °C

Procedure

(R)-Mandelic acid (20 g, 130 mmol) was dissolved in anhydrous pentane (200 mL, 1.7 mol). Pivaldehyde (13.6 g, 153 mmol) was added followed by trifluoromethanesulfonic acid (488 μL, 5.4 mmol). The mixture was allowed to reflux at 36° C. under nitrogen. After 5.5 hours, the mixture was allowed to cool to room temperature before stirring with 200 mL of an 8 wt % NaHCO3 solution for 10 minutes. Excess pentane was removed by rotary evaporation. The solids were collected by filtration and rinsed (100 mL water) while under vacuum filtration. The solids were dried overnight under high vacuum to yield 23.8 grams of intermediate (1a) as a white solid (88% purity).

Workup

  1. temperatureto cool to room temperature
  2. customExcess pentane was removed by rotary evaporation
  3. filtrationThe solids were collected by filtration
  4. washrinsed (100 mL water)
  5. filtrationwhile under vacuum filtration
  6. customThe solids were dried overnight under high vacuum

Sources & evidence

ORD record
ord-13739487671b49dab8723924d2189db6
Source dataset
uspto-grants-2013_07
Patent number
US08492407B2

Reaction notes

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