1,2-Dimethoxyethane → HCID 20336134, compound

HRID 1706504Notes

Reaction equation

HRID 1706504 reaction equation
Cl/[CH:2]=[CH:3]/[C:4](=[O:14])[C:5]([CH3:13])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].C(COC)OC.[Br-:21].[Li+]>CCOCC>[Br:21]/[CH:2]=[CH:3]/[C:4](=[O:14])[C:5]([CH3:13])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 82050Lithium BromideHCID 20336137HCID 20336137, compound

Product 1

HCID 20336134HCID 20336134, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 14 g. of 1-chloro-4-methyl-4- phenyl-1-trans-1-penten-3-one in 90 ml. of dimethoxyethane was treated with 24 g. of lithium bromide and refluxed for 24 hours. The mixture was diluted at 0° C. with ether, washed with brine, dried with MgSO4 and evaporated to dryness. The residue was redissolved in dimethoxyethane, treated with lithium bromide and refluxed for an additional 24 hours. After the exact same process was repeated thrice and the crude product was chromatographed on silica gel. Elution with 5% ethyl acetate in hexane afforded 8.9 g. of the title produce as a yellow oil, λmaxfilm 3.4, 5.88, 6.32, 6.66, 6.78, 6.88, 7.70, 9.25, 9.48, 9.98, 10.64, 12.80, 13.10 and 14.25 μ.

Workup

  1. washwashed with brine
  2. dry with materialdried with MgSO4
  3. customevaporated to dryness
  4. dissolutionThe residue was redissolved in dimethoxyethane
  5. additiontreated with lithium bromide
  6. temperaturerefluxed for an additional 24 hours
  7. customthe crude product was chromatographed on silica gel
  8. washElution with 5% ethyl acetate in hexane
  9. customafforded 8.9 g
  10. customof the title produce as a yellow oil, λmaxfilm 3.4, 5.88, 6.32, 6.66, 6.78, 6.88, 7.70, 9.25, 9.48, 9.98, 10.64, 12.80, 13.10 and 14.25 μ

Sources & evidence

ORD record
ord-f9a1c98f870e46f8b61679a7eb086329
Source dataset
uspto-grants-1980_06
Patent number
US04207419

Reaction notes

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