Diethyl Ether → HCID 13083371, compound

HRID 1194448Notes

Reaction equation

HRID 1194448 reaction equation
[CH:1]([NH:4]C(C)C)(C)C.[CH2:8]([Li])CCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2(CC#N)[CH2:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.CI.CCO[CH2:32][CH3:33]>O1CCCC1.CCCCCC.O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2([C:32]([CH3:33])([CH3:8])[C:1]#[N:4])[CH2:23][CH2:22][CH2:21]2)=[CH:18][CH:19]=1

Participants

9

Reactant 5

HCID 3283Diethyl Ether2×HCID 6328Methyl iodide2×HCID 7912DiisopropylamineHCID 13083370HCID 13083370, compoundHCID 178418339Butyllithium

Product 1

HCID 13083371HCID 13083371, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent5×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of di-isopropylamine (16.5 g) in dry tetrahydrofuran (50 ml) was stirred under nitrogen at a temperature of 0° C. and a 1.6M solution of n-butyllithium in hexane (100 ml) added dropwise. The reaction mixture was stirred for 30 minutes and then cooled to -78° C. A solution of 2-[1-(4-chlorophenyl)cyclobutyl]acetonitrile (9.5 g) prepared as described above in dry tetrahydrofuran (25 ml) was added dropwise. The temperature of the mixture was allowed to rise to 0° C. and the mixture was stirred for ten minutes before a solution of methyl iodide (10 ml) in tetrahydrofuran (10 ml) was added. Tetrahydrofuran (75 ml) was added to give a homogeneous solution and a further solution of methyl iodide (4 ml) in tetrahydrofuran (10 ml) added. The mixture was stirred at ambient temperature for two hours and then water (50 ml) added. The aqueous phase was washwed with ether and the ether combined with the organic phase of the reaction mixture. The combined organic phases were washed three times with 5N hydrochloric acid, three times with water, dried and evaporated to yield an oil which solidified and was recrystallised from industrial methylated spirit to give 2-[1-(4-chlorophenyl)cyclobutyl]-2-methylpropionitrile (m.p. 73°-75° C.).

Workup

  1. additionwas added dropwise
  2. customto rise to 0° C.
  3. additionwas added
  4. customto give a homogeneous solution
  5. stirringThe mixture was stirred at ambient temperature for two hours
  6. washThe combined organic phases were washed three times with 5N hydrochloric acid, three times with water
  7. customdried
  8. customevaporated
  9. customto yield an oil which
  10. customwas recrystallised from industrial methylated spirit

Sources & evidence

ORD record
ord-aead578c1ad247ee89d95706f5cc04db
Source dataset
uspto-grants-1989_03
Patent number
US04814352

Reaction notes

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