Tetrahydrofuran → HCID 178448139, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][SiH:13](Cl)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH2:17]1[CH2:21]O[CH2:19][CH2:18]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C@H:10]2[CH2:15][CH2:14][Si@H:13]([C@H:17]3[CH2:21][CH2:4][C@H:3]([CH2:2][CH2:7][CH3:6])[CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1Participants
3
Procedure
4.1 g (20 mmols) of 4-n-propylcyclohexyl 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 5.2 g (20 mmols) of 4-(4-fluorophenyloxymethyl)-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 and the cyclohexane ring. The product was after-treated by a usual manner and isolated through column chromatography to obtain 6.1 g (yield: 87%) of the intended trans-trans isomer product.
Sources & evidence
- ORD record
- ord-71a8d51a195c470895b34546a491d73c
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05641430
Reaction notes
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