Methyl pyruvate → Methyl 2-Methyl-5,5-diphenyl[1,3]dioxane-2-carboxylate

HRID 1859757Notes

Reaction equation

HRID 1859757 reaction equation
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH2:10][OH:11])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:23][CH3:24])(=[O:22])[C:19]([CH3:21])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH3:21][C:19]1([C:18]([O:23][CH3:24])=[O:22])[O:9][CH2:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:10][O:11]1

Participants

4

Reactant 3

HCID 11748Methyl pyruvateHCID 14812Phosphorus oxide (P4O10)HCID 4104452,2-Diphenylpropane-1,3-diol

Product 1

HCID 15428822Methyl 2-Methyl-5,5-diphenyl[1,3]dioxane-2-carboxylateYield 22.4%

Procedure

A mixture of 22.8 g (0.1 M) of 2,2-diphenyl-1,3-propanediol and 100 g (0.98 M) of methyl pyruvate is brought to 70° C. in a 500 ml round-bottomed flask under a nitrogen atmosphere. 22.4 g (0.156 M) of P2O5 are added portionwise. An exothermic reaction takes place and the temperature rises to 98° C. The mixture is allowed to return to room temperature and is poured slowly into ice-cold water. This mixture is extracted with methylene chloride and the extracts are washed with sodium hydroxide and water. The extracts are concentrated and the residue is chromatographed by flash chromatography (70 CH2Cl2/50 cyclohexane eluent). The product is then recrystallized from 40 ml of diisopropyl ether. 7 g of a product of m.p. 116° C. are obtained.

Workup

  1. customis brought to 70° C. in a 500 ml round-bottomed flask under a nitrogen atmosphere
  2. customAn exothermic reaction
  3. customrises to 98° C
  4. customto return to room temperature
  5. additionis poured slowly into ice-cold water
  6. extractionThis mixture is extracted with methylene chloride
  7. washthe extracts are washed with sodium hydroxide and water
  8. concentrationThe extracts are concentrated
  9. customthe residue is chromatographed by flash chromatography (70 CH2Cl2/50 cyclohexane eluent)
  10. customThe product is then recrystallized from 40 ml of diisopropyl ether

Sources & evidence

ORD record
ord-d44e178896d34d1297817129dfb18f97
Source dataset
uspto-grants-2003_03
Patent number
US06528538B1

Reaction notes

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