Water → HCID 21487590, compound

HRID 1414481Notes

Reaction equation

HRID 1414481 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][CH:6]=1)[CH3:4].Br[CH2:13][CH2:14][CH:15]([CH3:23])[CH2:16][CH2:17][CH:18]1[O:22][C:19]1([CH3:21])[CH3:20].[OH2:24]>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[O:22]1[C:19]([CH3:21])([CH3:20])[CH:18]1[CH2:17][CH2:16][CH:15]([CH3:23])[CH2:14][CH2:13][O:24][C:5]1([CH2:3][CH3:4])[CH:10]=[CH:9][CH:8]=[CH:7][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 312424-EthylphenolHCID 155027843-(5-Bromo-3-methylpentyl)-2,2-dimethyloxirane

Product 1

HCID 21487590HCID 21487590, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

In a 1.0 liter four-necked flask fitted with a reflux condenser a mechanical stirrer, dropping funnel and a gas inlet tube is placed 50 ml of dry tetrahydrofurane and 1.5 g NaH (prepared from 50% suspension through washing with tetrahydrofuran). 7.5g of p-ethylphenol in 50 ml of tetrahydrofuran is then added dropwise with stirring while a nitrogen atmosphere is maintained in the flask. The mixture is stirred until solution of NaH is complet, and 13.0 g. 1-bromo-6,7-epoxy-3,7-dimethyloctane in 20 ml hexamethylphosphoric triamide is added dropwise and with stirring. The resulting mixture is boiled under reflux, with stirring for 3 hours. After the addition of 1.0 liter of water the mixture is extracted with 0.5 liters of hexane and hexane extract is dried over sodium sulfate, filtered and concentrated in vacuo with water aspirator. The product was chromatographed on silica gel, fractions eluted with a mixture hexane-ethyl-acetate (9:1 parts by volume) afforded 6,7-Epoxy-1-(1-ethylphenoxy)-3,7-dimethyl-octane nD24 - 1,4973.

Workup

  1. customIn a 1.0 liter four-necked flask fitted with a reflux condenser a mechanical stirrer
  2. temperatureis maintained in the flask
  3. stirringwith stirring
  4. temperatureunder reflux
  5. stirringwith stirring for 3 hours
  6. extractionis extracted with 0.5 liters of hexane and hexane
  7. extractionextract
  8. dry with materialis dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo with water aspirator
  11. customThe product was chromatographed on silica gel, fractions
  12. washeluted with a mixture hexane-ethyl-acetate (9:1 parts by volume)

Sources & evidence

ORD record
ord-7fdee69ded6245889af95c3aab3fb37b
Source dataset
uspto-grants-1977_01
Patent number
US04001339

Reaction notes

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