Acetone → HCID 87299829, compound

HRID 1045056Notes

Reaction equation

HRID 1045056 reaction equation
C(C1(C(O)=O)[CH2:8][CH2:7][CH:6]([CH:9]([CH3:11])[CH3:10])[CH2:5][CH2:4]1)C.[Li]C.[CH3:17][C:18]([CH3:20])=[O:19].[CH2:21]1[CH2:26]NC(=O)C1.[Br:27][Br-]Br>C(OCC)C.CO>[Br:27][CH2:17][C:18]([C:20]1([CH2:26][CH3:21])[CH2:4][CH2:5][CH:6]([CH:9]([CH3:10])[CH3:11])[CH2:7][CH2:8]1)=[O:19]

Participants

6

Reactant 3

HCID 180AcetoneHCID 65425682HCID 65425682, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 87299829HCID 87299829, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-Ethyl-4-isopropyl-cyclohexanecarboxylic acid (800 mg, 4.7 mmol) in ethyl ether (about 20 mL) at 0° C. was treated with MeLi (5.5 mL in ethyl ether; 8.8 mmol) and stirred overnight at RT following a method analogous to General Procedure A1 to generate the corresponding methyl ketone (600 mg) after quenching the reaction with water, aq extractive workup, evaporation of the solvent and purification of the crude ketone. The resulting ketone (600 mg, 3 mmol) was treated with pyrrolidone hydrotribromide (1.6 g, 3.3 mmol) in MeOH (10 mL) and stirred at RT overnight following a method analogous to General Procedure B1 to produce 2-bromo-1-(1-ethyl-4-isopropyl-cyclohexyl)-ethanone (600 mg, 55% overall yield for two steps) after evaporation of the solvent, extractive workup with EtOAc and aq sodium bicarbonate, drying of the organic portion and removal of the solvent under vacuum.

Workup

  1. customafter quenching
  2. customthe reaction
  3. customwith water, aq extractive workup, evaporation of the solvent and purification of the crude ketone
  4. stirringstirred at RT overnight

Sources & evidence

ORD record
ord-126a40f4b25643778eaf4f7480a1901d
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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