Bromocyclopentane → HCID 13084235, compound

HRID 2052554Notes

Reaction equation

HRID 2052554 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]2[O:14][C:13](=[O:15])[NH:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H-].[Na+].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C)C=O>[CH:18]1([O:1][C:2]2[CH:3]=[C:4]([CH:10]3[O:14][C:13](=[O:15])[NH:12][CH2:11]3)[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 20376210HCID 20376210, compound

Product 1

HCID 13084235HCID 13084235, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.2 mmol of 5-(3-hydroxy-4-methoxyphenyl)-2-oxazolidinone is dissolved in 10 ml. of absolute dimethylformamide and stirred with 7.9 mmol of sodium hydride for 1 hour at 50°. After cooling, the mixture is combined with 8.6 mmol of cyclopentyl bromide and then agitated for 2 hours at 80°. After the reaction is terminated, the dimethylformamide is withdrawn under vacuum at 40°. The residue is taken up in 100 ml. of 2 N sodium hydroxide solution and extracted three times with 150 ml. of chloroform. The combined chloroform phases are washed with water, dried, filtered, and concentrated. The residue is recrystallized from ethyl acetate/ether, thus obtaining in a 70% yield 5-(3-cyclopentoxy-4-methoxyphenyl)-2-oxazolidinone, m.p. 111°-112°.

Workup

  1. temperatureAfter cooling
  2. customAfter the reaction is terminated
  3. customthe dimethylformamide is withdrawn under vacuum at 40°
  4. extractionof 2 N sodium hydroxide solution and extracted three times with 150 ml
  5. washThe combined chloroform phases are washed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-79b0c582318e40c7adfd446e6268fd33
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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