Tetrahydrofuran → HCID 178444456, compound
Reaction equation
Cl[Si@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([F:17])[F:16])=[C:10]([F:18])[CH:9]=2)[CH2:4][CH2:3]1.[CH2:19]1[CH2:23]O[CH2:21][CH2:20]1>>[F:18][C:10]1[CH:9]=[C:8]([C@H:5]2[CH2:6][CH2:7][Si@H:2]([CH2:21][CH2:20][CH2:19][CH2:23][C@H:19]3[CH2:23][CH2:3][C@H:4]([CH2:5][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:21][CH2:20]3)[CH2:3][CH2:4]2)[CH:13]=[CH:12][C:11]=1[O:14][CH:15]([F:17])[F:16]Participants
3
Procedure
28.9 g (0.1 mol) of trans-4-(4-bromobutyl)-1-n-pentylcyclohexane was dropped in a mixture of 2.5 g (0.11 mols) of magnesium and 300 ml of THF to obtain a Grignard reagent. The resultant solution was then dropped in a solution, in 500 ml of THF, of 29.5 g (0.1 mol) of 4-(trans-4-chloro-4-silacyclohexyl)-2-fluoro-1-difluoromethoxybenzene. The resultant product consisted of a mixture of trans and cis isomers with respect to the cyclohexane ring. The product was subjected to ordinary aftertreatments to obtain trans-4-(4-(trans-4-(3-fluoro-4-difluoromethoxyphenyl)-1-silacyclohexyl)butyl)-1-n-pentylcyclohexane, followed by isolation through chromatography to obtain 41.8 g (yield: 89%) of the intended trans isomer product.
Sources & evidence
- ORD record
- ord-c63f456aff8245a1bc480840ea41f61c
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665271
Reaction notes
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