18-Crown-6 → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile
Reaction equation
Br[CH:2]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[CH:3](Br)[C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH2:8][C:7]([CH3:17])([CH3:16])[C:6]=2[CH:5]=1.C1OCCOCCOCCOCCOCCOC1>>[CH3:14][C:10]1([CH3:15])[CH2:9][CH2:8][C:7]([CH3:16])([CH3:17])[C:6]2[CH:5]=[C:4]([C:3]#[C:2][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[CH:13]=[CH:12][C:11]1=2Participants
Conditions
- Temperature
- 50 °C
Procedure
6.7 g (0.014 mole) of 1,2-dibromo-1-(4-cyanophenyl)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethane (cf. Example 6a) were suspended in 26 ml of petroleum ether. After the addition of 3.2 g (0.028 mole) of potassium tert.-butylate, the temperature of the reaction mixture increased to 50° C. The mixture was refluxed for 1 hour, 20 mg (0.1 mole) of 18-crown-6 were added, and refluxing was continued for a further 10 hours. Thereafter, the mixture was poured onto 500 ml of ice water and extracted twice with petroleum ether, and the organic phase was washed with water, dried over sodium sulfate and evaporated down under reduced pressure to give 4.3 g of crude product. Recrystallization from ethanol gave 1.9 g (43%) of the title compound of melting point 166° C.
Workup
- temperatureThe mixture was refluxed for 1 hour
- temperaturerefluxing
- extractionextracted twice with petroleum ether
- washthe organic phase was washed with water
- dry with materialdried over sodium sulfate
- customevaporated down under reduced pressure
- customto give 4.3 g of crude product
- customRecrystallization from ethanol
Sources & evidence
- ORD record
- ord-fe54eb5bf7604a83aae193e795dd60c2
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806558
Reaction notes
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