HCID 137327395, compound → HCID 178447779, compound

HRID 1684448Notes

Reaction equation

HRID 1684448 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][CH:11]2[CH2:16][CH2:15][SiH:14](Cl)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:16][CH2:15][Si@H:14]([CH2:6][CH2:7][CH2:2][CH2:3][CH3:4])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 1

HCID 137327395HCID 137327395, compound

Product 1

HCID 178447779HCID 178447779, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g (20 mmols) of n-pentyl bromide was dropped in a mixture of 0.5 g of magnesium (21 mmols) and 50 ml of tetrahydrofuran (hereinafter referred to simply as THF) to obtain a Grignard reagent. Subsequently, the solution was dropped in 50 ml of a THF solution of 5.5 g (20 mmols) of 4-(3,4-difluorophenyloxymethyl)-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 5.6 g (yield: 89%) of the intended trans isomer product The results of measurement of a phase transition temperature and the IR analysis are shown below.

Sources & evidence

ORD record
ord-de8c5867eb7140799a3004d0be85c902
Source dataset
uspto-grants-1997_06
Patent number
US05641430

Reaction notes

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