Diethyl Ether → HCID 9995583, compound

HRID 359546Notes

Reaction equation

HRID 359546 reaction equation
[CH:1]1([C:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:10])[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CNC(=O)C1.[Br:24][Br-]Br.CCOCC>O1CCCC1>[Br:24][CH2:9][C:8](=[O:10])[C:7]([OH:17])([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 15030057HCID 15030057, compound

Product 1

HCID 9995583HCID 9995583, compoundYield 1,158.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Cyclohexyl-1-hydroxy-1-phenyl-2-propanone (2.83 g, 12.2 mmole) was added to 50 mL of dry tetrahydrofuran (THF). The solution was stirred and a solution of pyrrolidone hydrotribromide (6.08 g, 12.3 mmole) in 125 mL of dry THF was added dropwise over a period of 2 hours. After being refluxed for 4 hours, the reaction mixture was cooled. Ether was added and the solution washed twice with water and dried over magnesium sulfate. Upon evaporation of the solution to dryness, an orange oil was isolated. The product was purified by flash column chromatography (silica, hexane/ethyl acetate (99:1 followed by 95:5) to afford 3-bromo-1-hydroxy-1-cyclohexyl-1-phenyl-2-propanone (1 44 g, 37.7%). NMR (CDCl3) 1.0-2.0 (m, 10 H), 2.4 (m, 1 H), 3.5 (s, 1 H), 4.1 (s, 1 H), 7.2-7.6 (m, 5 H).

Workup

  1. temperatureAfter being refluxed for 4 hours
  2. temperaturethe reaction mixture was cooled
  3. washthe solution washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. customUpon evaporation of the solution to dryness
  6. customan orange oil was isolated
  7. customThe product was purified by flash column chromatography (silica, hexane/ethyl acetate (99:1 followed by 95:5)

Sources & evidence

ORD record
ord-4026f93f5708437f8d2426a446909ee6
Source dataset
uspto-grants-1991_03
Patent number
US05001160

Reaction notes

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