Isopropyl iodide → HCID 66934326, compound

HRID 2093298Notes

Reaction equation

[CH:1]([CH:4]1[C:8](=[O:9])[C:7]([CH3:11])([CH3:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:12]C1(C)CCCCC1=O.C([N-]C(C)C)(C)C.[Li+].CN1C(=O)N(C)CCC1.IC(C)C>>[CH:1]([CH:4]1[C:8](=[O:9])[C:7]([CH3:10])([CH3:11])[CH2:6][CH2:5][CH2:12]1)([CH3:2])[CH3:3]

Participants

Reactant 5

HCID 6362Isopropyl iodide

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-

HCID 1369292,2-Dimethylcyclohexan-1-one

HCID 2724682Lithium diisopropylamide

HCID 66934379HCID 66934379, compound

Product 1

HCID 66934326HCID 66934326, compoundYield 78%

Procedure

As described in Example 3 for preparation of 5-isopropyl-2,2-dimethylcyclopentanone, from 2,2-dimethylcyclohexanone (12.6 g, 110 mmol), lithium diisopropylamide solution (2 M in THF, 55.0 ml, 110 mmol), DMPU (14.1 g, 110 mmol) and 2-iodopropane (25.5 g, 150 mmol), 6-isopropyl-2,2-dimethylcyclohexanone (13.1 g, 78%) was obtained after standard workup and purification by silica gel FC (pentane/Et2O, 6:4, Rf=0.26).

Sources & evidence

ORD record: ord-2afb819559994704aa1bd3f346a4f3b2
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445424B2

Reaction notes

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