Formaldehyde → HCID 57282655, compound

HRID 1666942Notes

Reaction equation

HRID 1666942 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11](O)=O)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCCCC1.C=O>CCO>[CH:1]1([CH2:6][C:7](=[CH2:11])[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 55250614(Cyclopentylmethyl)propanedioic acid

Product 1

HCID 57282655HCID 57282655, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-cyclopentylmethyl-malonic acid (24.90 g, 133.7 mmol), piperidine (15.9 mL, 160.8 mmol), 37% aqueous formaldehyde (51.0 mL, 647.2 mmol), and EtOH (250 mL) is stirred at reflux for 16 hours. The reaction is quenched with 1N HCl to a pH=1, and the mixture is extracted with EtOAc. The EtOAc layers are combined, dried over Na2SO4, and concentrated. The crude product is purified by flash chromatography (SiO2, 10% acetone in DCM), which gives 2-cyclopentylmethyl-acrylic acid (17.65 g, 86% yield) as an oil.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe reaction is quenched with 1N HCl to a pH=1
  3. extractionthe mixture is extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography (SiO2, 10% acetone in DCM), which

Sources & evidence

ORD record
ord-5ed42cc1c20c446f960145e89576667c
Source dataset
uspto-grants-2011_10
Patent number
US08044199B2

Reaction notes

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