1,5-Dibromopentane → HCID 54472139, compound

HRID 329257Notes

Reaction equation

HRID 329257 reaction equation
[H-].[K+].O1CCOCC1.[CH:9]([S:12][CH2:13][S:14](=[O:18])[CH:15]([CH3:17])[CH3:16])([CH3:11])[CH3:10].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br>C(Cl)Cl>[CH:9]([S:12][C:13]1([S:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 81001,5-DibromopentaneHCID 312751,4-DioxaneHCID 82127Potassium hydrideHCID 12426219HCID 12426219, compound

Product 1

HCID 54472139HCID 54472139, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium hydride (995 mg) was suspended in 15 ml. of dioxane, and with ice cooling, 1.804 g of formaldehyde diisopropyl mercaptal S-oxide was added gradually. The mixture was stirred for 1 hour with ice cooling, and then 2.411 g of 1,5-dibromopentane was added. Then, the mixture was stirred for 18 hours at room temperature. Methylene chloride (100ml) was added, and the isoluble matter was separated by filtration. After the evaporation of the filtrate at reduced pressure, the residue was separated by column chromatography (basic alumina, eluted with benzene, methylene chloride, and ethyl acetate) to afford 1.463 g of cyclohexanone diisopropyl mercaptal S-oxide as a colorless oil. The yield was 59%. The physical properties and the results of elemental analysis were as follows:

Workup

  1. stirringThen, the mixture was stirred for 18 hours at room temperature
  2. customthe isoluble matter was separated by filtration
  3. customAfter the evaporation of the filtrate at reduced pressure
  4. customthe residue was separated by column chromatography (basic alumina, eluted with benzene, methylene chloride, and ethyl acetate)

Sources & evidence

ORD record
ord-ac3f66267eb94e6b8dd673b63e31d3f2
Source dataset
uspto-grants-1977_04
Patent number
US04020171

Reaction notes

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