Cyclohexyl bromide → HCID 15752887, compound

HRID 1087590Notes

Reaction equation

HRID 1087590 reaction equation
[Mg].[CH:2]1(Br)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:9]([C:17]([O:19][C:20]([CH3:24])([CH3:23])[C:21]#[CH:22])=[O:18])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1.O>[CH:2]1([C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([OH:16])[C:17]([O:19][C:20]([CH3:24])([CH3:23])[C:21]#[CH:22])=[O:18])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 7960Cyclohexyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11458583HCID 11458583, compound

Product 1

HCID 15752887HCID 15752887, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent, prepared from 3.38 g magnesium and 2.27 g cyclohexyl bromide in anhydrous THF in the usual way, was added dropwise under a nitrogen gas stream to a solution of 1,1-dimethyl-2-propynyl benzoylformate in anyhdrous THF under ice cooling, and stirring was continued for 18 hours under cooling with water. A solution of 7.5 g ammonium chloride in 30 ml water was then added under ice cooling. The separated organic layer was collected, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily residue was purified by silica gel column chromatography (Wako Gel C-200; 1:15 mixture of ethyl acetate and n-hexane), giving 17.6 g of the objective compound as oil.

Workup

  1. customThe separated organic layer was collected
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe oily residue was purified by silica gel column chromatography (Wako Gel C-200; 1:15 mixture of ethyl acetate and n-hexane)

Sources & evidence

ORD record
ord-86d1e4da6d424a448e9e10706db6284a
Source dataset
uspto-grants-1991_07
Patent number
US05036098

Reaction notes

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