Bromocyclopentane → HCID 19025756, compound

HRID 1975720Notes

Reaction equation

HRID 1975720 reaction equation
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]#[N:23])=[CH:17][CH:16]=1.[H][H].[CH:26]1(Br)[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C=O)C>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:22]#[N:23])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 14501730HCID 14501730, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19025756HCID 19025756, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.6 g (80 % pure) of sodium hydride (0.02 mol) is suspended in 40 ml of absolute DMF at 0° C., and 5.5 g (0.02 mol) of the compound from Example I in 20 ml of DMF are added dropwise. Evolution of hydrogen starts. During this process, the temperature rises to room temperature. The mixture is subsequently stirred at room temperature for a further hour and then cooled to 0° C., and 3 g (0.02 mol) of cyclopentyl bromide are added dropwise. The mixture is allowed to react further overnight and then concentrated to dryness in vacuo, and the residue is extracted by stirring with 180 ml of water/methylene chloride (1: 1) . The organic phase is separated off, dried and concentrated to a small volume, and the residue is separated by column chromatography (silica gel 60, mobile phase: toluene/ethyl acetate 9:1).

Workup

  1. customrises to room temperature
  2. temperaturecooled to 0° C.
  3. customto react further overnight
  4. concentrationconcentrated to dryness in vacuo
  5. extractionthe residue is extracted
  6. stirringby stirring with 180 ml of water/methylene chloride (1: 1)
  7. customThe organic phase is separated off
  8. customdried
  9. concentrationconcentrated to a small volume
  10. customthe residue is separated by column chromatography (silica gel 60, mobile phase: toluene/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-a2f4ccb95d334d05a3a8620ac446d4dd
Source dataset
uspto-grants-1994_02
Patent number
US05288733

Reaction notes

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