Malonic Acid → HCID 6105229, compound

HRID 1506962Notes

Reaction equation

HRID 1506962 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].C(=O)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CS(C)=O.O.CC(O)=O.N1CCCCC1>[C:11]1([CH2:10]/[CH:9]=[CH:1]/[CH2:2][C:3]([OH:5])=[O:4])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 2

HCID 867Malonic AcidHCID 7707Benzenepropanal

Product 1

HCID 6105229HCID 6105229, compoundYield 79.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of malonic acid (17.06 g, 163.96 mmol) in DMSO (65 mL) was treated with a solution of AcOH (0.1 mL, 1.49 mmol) and piperidine (0.15 mL, 1.49 mmol) in DMSO (4 mL). The reaction solution was warmed to 65° C. and hydrocinnamaldehyde (10 g, 74.53 mmol) was added dropwise within 1.5 hr. After the addition ended, the reaction mixture was stirred for further 2 h at 65° C. The solution was cooled to room temperature, taken up in H2O and extracted with Et2O. The combined organic extracts were washed with 5% aqueous KHSO4 and brine, dried over MgSO4, and evaporated to dryness. The crude compound was purified by a silica gel column to produce the title compound (10.4 g, 75˜90%)

Workup

  1. additionAfter the addition
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with Et2O
  4. washThe combined organic extracts were washed with 5% aqueous KHSO4 and brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-aac21ea6ff6f4cb78f51bb4ad659f72b
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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