Water → HCID 86748404, compound
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[F:30][C:31]1[CH:32]=[C:33]([CH2:39][CH2:40][CH:41]2[CH2:46][CH2:45][C:44](=O)[CH2:43][CH2:42]2)[CH:34]=[C:35]([F:38])[C:36]=1[F:37].O>C1COCC1>[F:30][C:31]1[CH:32]=[C:33]([CH2:39][CH2:40][CH:41]2[CH2:46][CH2:45][C:44](=[CH:2][O:3][CH3:4])[CH2:43][CH2:42]2)[CH:34]=[C:35]([F:38])[C:36]=1[F:37]Participants
Conditions
- Temperature
- 0 °C
Procedure
A suspension of methoxymethyltriphenylphosphonium chloride (112.3 g) in THF (300 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (45.4 g) little by little while cooling at 0° C., stirring the reaction solution at room temperature for one hour, dropwise adding 4-(2'-(3",4",5"-trifluorophenyl)ethyl)cyclohexanone (70 g)in THF (200 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (500 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO4, concentrating under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(2'-(3",4",5"-trifluorophenyl)ethyl)methoxymethylenecyclohexane (53.7 g).
Workup
- stirringstirring the reaction solution at room temperature for one hour
- stirringfurther stirring for 2 hours
- customafter completion of the reaction
- extractionextracting with ethyl acetate (500 ml)
- dry with materialdrying the organic layer over anhydrous MgSO4
- concentrationconcentrating under reduced pressure
Sources & evidence
- ORD record
- ord-f7895341675b4538bdbd5ca979747adc
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05382379
Reaction notes
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