HCID 178418348, compound → HCID 178468160, compound

HRID 1045050Notes

Reaction equation

HRID 1045050 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][Li]>C(OCC)C>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11](=[O:13])[CH3:14])[CH2:9][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 178418348HCID 178418348, compoundHCID 178445658HCID 178445658, compound

Product 1

HCID 178468160HCID 178468160, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To trans-4-tert-butyl-cyclohexanecarboxylic acid (921 mg, 5.0 mmol) in ethyl ether (35 mL) was added methyl lithium (1.6 M in ethyl ether, 7.1 mL, 11.4 mmol) to produce 1-(trans-4-tert-butyl-cyclohexyl)-ethanone (769 mg, 4.22 mmol, 84%) following a method analogous to General Procedure A1. Workup involved treatment of the reaction mixture with water (50 mL), and the organic portion was washed with aq NaHCO3 and then brine, and dried over sodium sulfate. Solvent evaporation under reduced pressure gave the crude methyl ketone (769 mg). This crude ketone product was converted into the corresponding 2-bromoketone (525 mg, 2.01 mmol) following a method analogous to General Procedure B2 using bromine (0.228 mL, 4.43 mmol) and MeOH (about 10 mL).

Sources & evidence

ORD record
ord-a16907afb0994c99b2325f4e3fa491cd
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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