Water → 1-(Pyrrolidin-1-yl)prop-2-en-1-one

HRID 703098Notes

Reaction equation

HRID 703098 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[NH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C.O>C(OCC)C>[O:4]=[C:1]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 1820551-(Pyrrolidin-1-yl)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-50 °C

Procedure

Acryloyl chloride (9 g, 0.1 mole) was added by syringe to ethyl ether (40 ml) and the solution cooled to -50° C. A solution of pyrrolidine (7.1 g, 0.1 mole) in ethyl ether (20 ml) was added dropwise. A solution of triethylamine (15.3 ml) was added slowly over 10 minutes. The reaction was slowly allowed to warm to room temperature and stirred for 12 hours. Water (50 ml) was added, the layers were separated and the aqueous Iayer extracted with ethyl ether (100 ml) and methylene chloride (2×ml), and combined with the organic layer above, dried over sodium sulfate, filtered, and the solvents removed to give an oil. The product was purified by chromatography on silica. The structure was confirmed by NMR.

Workup

  1. temperatureto warm to room temperature
  2. customthe layers were separated
  3. extractionthe aqueous Iayer extracted with ethyl ether (100 ml) and methylene chloride (2×ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvents removed
  7. customto give an oil
  8. customThe product was purified by chromatography on silica

Sources & evidence

ORD record
ord-406cee76ecaa4fa5a93d9409f59d6c87
Source dataset
uspto-grants-1991_01
Patent number
US04981853

Reaction notes

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