Hydrochloric Acid → HCID 11736945, compound
Reaction equation
[CH2:1]([Zn]CC)C.FC(F)(F)C(O)=O.ICI.[CH2:16]1[O:33][C:19]2([CH2:24][CH2:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=3)=[CH:21][CH2:20]2)[O:18][CH2:17]1.Cl>C(Cl)Cl>[CH2:17]1[O:18][C:19]2([CH2:24][CH2:23][C:22]3([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=4)[CH:21]([CH2:1]3)[CH2:20]2)[O:33][CH2:16]1Participants
Conditions
- Temperature
- 0 °C
Procedure
Diethylzinc(1 M in hexane, 19 ml, 19 mmole) was mixed with 50 ml methylene chloride and the mixture was cooled to 0° C. Trifluoroacetic acid (2.1 g, 19 mmole) in 20 mL methylene chloride was added. The mixture was stirred at 0° C. for 20 minutes. Diiodomethane (5 g, 19 mmole) in 10 ml methylene chloride was then added, followed by 4-(3-cyanophenyl)-3-cyclohexene-1-one ethylene ketal (1.5 g, 6.2 mmole) in 20 mL methylene chloride. The mixture was stirred at room temperature overnight. 50 ml 1N hydrogen chloride solution was added to quench the reaction. The organic layer was separated, washed with water (2×50 mL) and dried over sodium sulfate. The product was purified by column using ethyl acetate/hexane (10/90) as the eluent to afford 6-(3-cyanophenyl)bicyclo[4.1.0]heptane-3-one ethylene ketal (0.8 g, 50%).
Workup
- stirringThe mixture was stirred at room temperature overnight
- customto quench
- customthe reaction
- customThe organic layer was separated
- washwashed with water (2×50 mL)
- dry with materialdried over sodium sulfate
- customThe product was purified by column
Sources & evidence
- ORD record
- ord-3a5540f5c82c49c6b69aeac46c2857b9
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348328B2
Reaction notes
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