Tetrahydrofuran → HCID 178460952, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH:17]3[CH2:22][CH2:21][SiH:20](Cl)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH2:24]1[CH2:28]OC[CH2:25]1>>[F:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C@H:17]3[CH2:22][CH2:21][Si@H:20]([CH2:25][CH2:24][CH3:28])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8]Participants
3
Procedure
2.5 g (20 mmols) of n-propyl bromide was dropped in a mixture of 0.5 g of magnesium (21 mmols) and 50 ml of THF to obtain a Grignard reagent. Subsequently, the solution was dropped in 50 ml of a THF solution of 7.2 g (20 mmols) of 4-(trans-4-(3,4-difluorophenyloxymethyl)cyclohexyl)-1-chloro-1-silacyclohexane to obtain a crude product. This product was found to be a mixture of trans and cis isomers with respect to the silacyclohexane ring. The product was after-treated by a usual manner and isolated through column chromatography to obtain 6.7 g (yield: 91%) of the intended trans-trans isomer product. The results of measurement of phase transition temperatures and the IR analysis are shown below.
Sources & evidence
- ORD record
- ord-cd1bdf12d848472e8f036fdd0d8bc79f
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05641430
Reaction notes
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