Iodoethane → HCID 67044939, compound

HRID 1045054Notes

Reaction equation

HRID 1045054 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]1)=[O:4].[Li+].[CH3:15][CH:16]([N-]C(C)C)C.ICC>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([CH2:15][CH3:16])[CH2:10][CH2:9][CH:8]([CH:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2724682Lithium diisopropylamideHCID 11019548HCID 11019548, compound

Product 1

HCID 67044939HCID 67044939, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Isopropyl-cyclohexanecarboxylic acid methyl ester (1.1 g, 6 mmol) was alkylated using a method analogous to General Procedure F using LDA (9 mmol) and iodoethane (1.4 g, 9 mmol) in THF (20 mL) at −78° C. to RT to produce 1-ethyl-4-isopropyl-cyclohexanecarboxylic acid methyl ester (1.0 g, 78% yield) as a mixture of isomers. Hydrolysis of this ester using KOH (12.5 mmol) in aqueous EtOH (1:1; 5 mL) at 150° C. for 2 hr in a pressurized vessel following a microwave method analogous to General Procedure G2 gave 1-ethyl-4-isopropyl-cyclohexanecarboxylic acid (800 mg, 86% yield) as a mixture of isomers after workup by evaporation of the solvent, treatment with aq 2 N HCl, extractive workup, and evaporation of the solvent.

Workup

  1. customat −78° C. to RT

Sources & evidence

ORD record
ord-d2f994a44e734a8b95135de81ddce57b
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

Loading…