Ammonium Chloride → HCID 68576919, compound

HRID 638789Notes

Reaction equation

HRID 638789 reaction equation
[Li+].CC([N-]C(C)C)C.[CH3:9][C:10]1[C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH:15]=1.[CH2:17](Br)[CH:18]=[C:19]([CH3:21])[CH3:20].[NH4+].[Cl-]>C1COCC1.CC(OC)(C)C>[CH3:9][C:10]1[C:11](=[O:16])[CH:12]([CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH2:13][CH2:14][CH:15]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 700922-Butene, 1-bromo-3-methyl-HCID 1368872-Cyclohexen-1-one, 2-methyl-HCID 2724682Lithium diisopropylamide

Product 1

HCID 68576919HCID 68576919, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of LDA (prepared from BuLi, 1.6 M in hexane, 75 ml, 0.12 mol and diisopropylamine, 12.2 g, 0.12 mol) in THF (50 ml) was added 2-methyl-cyclohex-2-enone (11.0 g, 0.1 mol) at −78° C. The mixture was stirred for 1 h at −78° C. and prenyl bromide 17.88 g, 0.12 mol) was added. The mixture was stirred over night, while the temperature was allowed to rise to room temperature. MTBE (50 ml) and sat. NH4Cl were added, the organic phase was separated and washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled in a Kugelrohr oven to yield 9.8 g (55%) of a slightly yellow oil.

Workup

  1. stirringThe mixture was stirred over night, while the temperature
  2. customto rise to room temperature
  3. customthe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was distilled in a Kugelrohr oven
  8. customto yield 9.8 g (55%) of a slightly yellow oil

Sources & evidence

ORD record
ord-f587ac21a9c84c1588cbdfb73e3c670e
Source dataset
uspto-grants-2010_04
Patent number
US07691802B2

Reaction notes

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