Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.C([Li])CCC.CCCCCC.[C:23]1(=[O:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[Cl-].[NH4+]>O1CCCC1>[C:10]([CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:23]1([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)#[N:11]Participants
Conditions
- Temperature
- -70 °C
Procedure
p-Methoxyphenylacetonitrile (50 gm, 0.3 mole) was added to dry tetrahydrofuran (250 ml) and the solution cooled to -70° C. under nitrogen. n-Butyl lithium in hexane (210 ml, 0.3 mole) was added dropwise, with stirring. The temperature was maintained below -50° C. and a yellow precipitate appeared. After the addition was complete, the reaction mixture was maintained below -50° C. for 30 minutes and cyclohexanone (35 ml, 0.3 mole) was added. After a further 45 minutes below -50° C. the temperature was allowed to rise to 0° C. and a saturated ammonium chloride solution was added. The layers were separated and the aqueous layer extracted with diethyl ether. The combined organic solution was washed with brine, dried over magnesium sulphate and evaporated. The product crystallized (25.2 gm, m.p. 125°-127° C.).
Workup
- temperatureThe temperature was maintained below -50° C.
- additionAfter the addition
- temperaturethe reaction mixture was maintained below -50° C. for 30 minutes
- customto rise to 0° C.
- customThe layers were separated
- extractionthe aqueous layer extracted with diethyl ether
- washThe combined organic solution was washed with brine
- dry with materialdried over magnesium sulphate
- customevaporated
- customThe product crystallized (25.2 gm, m.p. 125°-127° C.)
Sources & evidence
- ORD record
- ord-53b0532ff7824926866cd13eab492272
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04611078
Linked notes
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