Water → a,a-diMethyl-1-Pyrrolidineacetaldehyde

HRID 703101Notes

Reaction equation

HRID 703101 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:13][C:14](=[CH2:18])[C:15](Cl)=[O:16].O>C(OCC)C>[CH3:13][C:14]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:18])[CH:15]=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 53867504a,a-diMethyl-1-Pyrrolidineacetaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, pyrrolidine (3.55 g, 0.05 mole) was dissolved in ethyl ether (50 ml). Triethylamine (5.06 g, 0.05 mole) was added and the solution cooled to and maintained at 0° C. 2-Methylacryloyl chloride (5.22 g, 0.05 mole), dissolved in ethyl ether (50 ml) was added to the reaction and the solution stirred overnight. Water (50 ml) was added, the layers were separated and the aqueous layer extracted with ethyl ether. The extracts were concentrated and the resulting product dried (6.77 g). The structure was confirmed by NMR.

Workup

  1. temperaturethe solution cooled to and
  2. additionwas added to the reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer extracted with ethyl ether
  5. concentrationThe extracts were concentrated
  6. customthe resulting product dried (6.77 g)

Sources & evidence

ORD record
ord-484fbafbd97a4b05bc3625401c2cd7f1
Source dataset
uspto-grants-1991_01
Patent number
US04981853

Reaction notes

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