Methyl iodide → HCID 59518507, compound

HRID 1161614Notes

Reaction equation

HRID 1161614 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][C:3]1=[O:9].[CH:11]([N-]C(C)C)(C)C.[Li+].CI.[C:21](C#N)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)C.CN(C)P(N(C)C)(N(C)C)=O>[C:21]([CH:4]1[C:5](=[O:8])[CH:6]([CH3:11])[CH2:7][C:2]([CH3:10])([CH3:1])[C:3]1=[O:9])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11953PhenylglyoxylonitrileHCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 2724682Lithium diisopropylamide

Product 1

HCID 59518507HCID 59518507, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
0 °C

Procedure

Compounds of formula (V) can be prepared according to a first representative procedure, as follows: 4,4-dimethylcyclohexane-1,3-dione 7 (1 mole eq) (commercially available) is dissolved in anhydrous diethylether and hexamethylphosphoramide (solvent ratio, 20:1 respectively) under an atmosphere of nitrogen. The mixture is cooled to 0° C. and lithium diisopropylamide (2.1 mole eq) is added dropwise over 40 mins. The mixture is then stirred for a further 10 mins before the addition of methyl iodide (1 mole eq). The mixture is stirred for 12 h and then benzoyl cyanide (2 mole eq) is added and the mixture stirred for a further 24 h. The reaction was quenched with water and the ether layer partitioned and dried (Na2SO4). The solvent was removed and the residue subjected to SiO2 column chromatography (hexane/ethyl acetate) affording 1-benzoyl-3,3,5-trimethylcyclohexan-2,6-dione 8 (Scheme 4).

Workup

  1. stirringthe mixture stirred for a further 24 h
  2. customThe reaction was quenched with water
  3. customthe ether layer partitioned
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-e123d8d079e248a590a88205c0fa2c1b
Source dataset
uspto-grants-2010_10
Patent number
US07820209B2

Reaction notes

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