Tetrahydrofuran → HCID 178436223, compound

HRID 254462

Reaction equation

HRID 254462 reaction equation
CO[C:3]1[CH:8]=[CH:7][CH:6]=[C:5](OC)[C:4]=1/[CH:11]=[N:12]/[CH:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15].[CH2:20]([Li])[CH3:21].[CH2:23]1COC[CH2:24]1>C1CCCCC1.C1C=CC=CC=1>[CH2:23]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:20][CH3:21])[C:4]=1/[CH:11]=[N:12]/[CH:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH3:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 178491344HCID 178491344, compoundHCID 178506846HCID 178506846, compound

Product 1

HCID 178436223HCID 178436223, compound

Reagents, catalysts & solvents 1

HCID 18624872Benzene--cyclohexane (1/1)Solvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 16.0 g (61 mmol) [1-(2,6-dimethoxy-phenyl)-meth-(E)-ylidene]-(1-isopropyl-2-methyl-propyl)-amine in 80 ml dry THF cooled to −40° C. were added 364 ml of a 0.5M solution of ethyl lithium in cyclohexane/benzene drop-wise to keep temperature below −20° C. Then the mixture was stirred at −20° C. for further 30 min and the reaction quenched by addition of water. The aqueous phase was extracted with ethyl acetate, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated: 15.6 g (E)-[1-(2,6-diethyl-phenyl)-methylidene]-(1-isopropyl-2-methyl-propyl)-amine as colourless liquid: MS (EI): 259.2 (M+.), 216.3 ((M-(CH3)2CH)+.)), 160.1 (((M-(((CH3)2CH)2CH))+.), 100%).

Workup

  1. customtemperature below −20° C
  2. customthe reaction quenched by addition of water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined extracts washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dc4bb5f122174db290298dd15ddb2ef0
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Linked notes

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