Hydrochloric Acid → HCID 178444354, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[F:8].[Mg].[CH2:11]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]2[C:23](=O)[CH2:24][CH2:25][CH2:26][CH:27]=2)[CH2:18][CH2:17]1)[CH2:12][CH2:13][CH2:14][CH3:15].Cl.C([O:32]CC)C>>[CH2:11]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]2[CH2:23][CH2:24][C:25]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)([OH:32])[CH2:26][CH:27]=2)[CH2:18][CH2:17]1)[CH2:12][CH2:13][CH2:14][CH3:15]Participants
Procedure
A solution of 6.0 g of 3,4-difluorobromobenzene in 25 ml. of anhydrous diethyl ether was added dropwise under stirring at 10°-15° C. to 0.66 g of magnesium metal powder, followed by reaction at room temperature for 1 hour so that a Grignard reagent was formed. After 5 g of trans-4-pentylcyclohexylcyclohexenone were added under stirring at -10° to 0° C. to the thus-formed Grignard reagent, they were reacted at room temperature for additional 1 hour. After the completion of the reaction, diluted hydrochloric acid was added dropwise to the reaction mixture, followed by the extraction of the reaction mixture with diethyl ether. After the extract was washed with saturated NaCl, anhydrous sodium sulfate was added to dry the extract. The diethyl ether was distilled off under reduced pressure, whereby 1-(trans-4-pentylcyclohexyl)-4-(3,4-difluorophenyl)-4-hydroxy-cyclohexene was obtained as a crude reaction product.
Workup
- customwas formed
- customwere reacted at room temperature for additional 1 hour
- additionwas added dropwise to the reaction mixture
- extractionfollowed by the extraction of the reaction mixture with diethyl ether
- washAfter the extract was washed with saturated NaCl, anhydrous sodium sulfate
- additionwas added
- customto dry the extract
- distillationThe diethyl ether was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-69de5751fbcf45e999f5b7f29685de27
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05342546
Reaction notes
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