Diethyl Ether → HCID 20511711, compound

HRID 1164303Notes

Reaction equation

HRID 1164303 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)C.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].C(N(CC)CC)C>C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 120252-PyrrolidoneHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 20511711HCID 20511711, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

15.9 g. of p-benzyloxybenzoyl chloride, 500 ml. of absolute diethyl ether and 6.3 ml. of 2-pyrrolidinone are treated with 13.4 ml. of triethylamine at 0° C. to 10° C. while stirring. The mixture is stirred at reflux for 9 hours, then cooled down and treated at 0° C. with cold water and ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and evaporated. The residue is triturated with diethyl ether and the insoluble constituents are chromatographed over silica gel (particle size 0.2-0.5 mm). The constituents elutable with methylene chloride are triturated with diethyl ether. The insoluble constituents are filtered off and there is obtained 1-(p-benzyloxybenzoyl)-2-pyrrolidinone, having a melting point of 115°-117° C.

Workup

  1. temperatureat reflux for 9 hours
  2. temperaturecooled down
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue is triturated with diethyl ether
  7. customthe insoluble constituents are chromatographed over silica gel (particle size 0.2-0.5 mm)
  8. customThe constituents elutable with methylene chloride are triturated with diethyl ether
  9. filtrationThe insoluble constituents are filtered off

Sources & evidence

ORD record
ord-d6fbf48280fc45ce889bd6505b20a32a
Source dataset
uspto-grants-1983_01
Patent number
US04369139

Reaction notes

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