1-Hexanol → 5-(n-Hexyloxy)-pyrrolidin-2-one

HRID 1639046Notes

Reaction equation

HRID 1639046 reaction equation
[OH:1][CH:2]1[NH:6][C:5](=[O:7])[CH2:4][CH2:3]1.[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>>[CH2:8]([O:1][CH:2]1[NH:6][C:5](=[O:7])[CH2:4][CH2:3]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 81031-HexanolHCID 1941485-Hydroxy-2-pyrrolidone

Product 1

HCID 156965635-(n-Hexyloxy)-pyrrolidin-2-one

Conditions

Temperature
60 °C

Procedure

A mixture of 0.4 g of 5-hydroxy-pyrrolidin-2-one, 10 cm3 of n-hexanol and 0.2 g of Amberlite IR 120H is heated to 60° C. for 3 hours. The solvent is distilled off at 25° C. under 0.3 mbar. The residue is chromatographed on silica (eluent: ethyl acetate); 0.5 g of the residue is crystallized from hexane, and the expected product is obtained, m.p. 35°-37° C.

Workup

  1. distillationThe solvent is distilled off at 25° C. under 0.3 mbar
  2. customThe residue is chromatographed on silica (eluent: ethyl acetate)
  3. custom0.5 g of the residue is crystallized from hexane

Sources & evidence

ORD record
ord-311bf308e5814242ada371960acacaa2
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

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