Diethyl Ether → HCID 131711262, compound

HRID 1764041Notes

Reaction equation

HRID 1764041 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].C(OC(O[CH2:31][N:32]1[CH2:36][CH2:35][CH2:34][C:33]1=[O:37])C)C.[H-].[Na+].[CH3:40][CH2:41][O:42][CH2:43][CH3:44].S([O-])([O-])(=O)=[O:46].[NH4+].[NH4+].CN(C)[CH:54]=[O:55]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[CH2:41]([O:42][CH:43]([O:55][CH2:54][CH:34]1[CH2:35][CH2:36][N:32]([CH2:31][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:3]([O:2][CH3:1])=[O:46])[C:33]1=[O:37])[CH3:44])[CH3:40]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 6097028Ammonium SulfateHCID 131711259HCID 131711259, compound

Product 1

HCID 131711262HCID 131711262, compound

Procedure

A solution of 5.98 g of dl-5-[1-(ethoxy)ethoxymethyl]-2-pyrrolidone in 8 ml of dimethylformamide is added gradually to a mixture of 40 ml of dimethylformamide, 1.24 g of 65% sodium hydride (an oil dispersion; washed with n-hexane) and 6.41 g of potassium iodide. The addition is carried out in nitrogen gas under ice-cooling and stirring. The solution is stirred at room temperature for 2 hours and then at 50° C. for 20 minutes. After the solution is cooled to room temperature, 8.6 g of methyl 7-bromo-n-heptanoate are added thereto, and the mixture is stirred at 50° C. for 2 days. Insoluble materials are filtered off. The filtrate is evaporated at 60° to 75° C. under reduced pressure (4 mmHg) to remove solvent. The residue obtained is mixed with ether and an aqueous saturated ammonium sulfate solution, and the mixture is shaken. Then, the organic solvent layer is separated from the mixture, and the aqueous layer is extracted with ether. The organic solvent layer and ether extract are combined, washed with water saturated with ammonium sulfate, dried and then evaporated to remove solvent. The residue thus obtained is purified by silica gel chromatography [Solvent: ethylacetate-methanol (20:1)]. dl-5-[1-(Ethoxy)ethoxymethyl]-1-(6-methoxycarbonylhexyl)-2-pyrrolidone is obtained as yellowish brown oil. Yield: 8.16 g

Workup

  1. washwashed with n-hexane) and 6.41 g of potassium iodide
  2. additionThe addition
  3. temperaturecooling
  4. stirringThe solution is stirred at room temperature for 2 hours
  5. addition8.6 g of methyl 7-bromo-n-heptanoate are added
  6. stirringthe mixture is stirred at 50° C. for 2 days
  7. filtrationInsoluble materials are filtered off
  8. customThe filtrate is evaporated at 60° to 75° C. under reduced pressure (4 mmHg)
  9. customto remove solvent
  10. customThe residue obtained
  11. customThen, the organic solvent layer is separated from the mixture
  12. extractionthe aqueous layer is extracted with ether
  13. extractionThe organic solvent layer and ether extract
  14. washwashed with water saturated with ammonium sulfate
  15. customdried
  16. customevaporated
  17. customto remove solvent
  18. customThe residue thus obtained
  19. customis purified by silica gel chromatography [Solvent: ethylacetate-methanol (20:1)]

Sources & evidence

ORD record
ord-c70b218da6f94aa3b33940decfce7bae
Source dataset
uspto-grants-1978_09
Patent number
US04113873

Reaction notes

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