HCID 131719280, compound → HCID 178447749, compound

HRID 1439824Notes

Reaction equation

HRID 1439824 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH2:3][CH2:4][CH3:5].Cl[SiH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[CH2:11][CH2:10]1>O1CCCC1>[F:24][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][C@H:12]2[CH2:13][CH2:14][Si@H:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:10][CH2:11]2)[CH:22]=[CH:21][C:20]=1[F:23]

Participants

4

Reactant 2

HCID 131719280HCID 131719280, compoundHCID 178445869HCID 178445869, compound

Product 1

HCID 178447749HCID 178447749, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

60 ml of a THF solution of 2.0M n-pentylmagnesium chloride was dripped into a mixture of 27.5 g (100 mmol) of 1-chloro-4-(2-(3,4-difluorophenyl)ethyl)-1-silacyclohexane and 200 ml of tetrahydrofuran (hereafter referred to as "THF"). The silacyclohexane rings of the target product thus obtained were a mixture of trans isomers and cis isomers. After a conventional after treatment, they were separated by means of chromatography to obtain 21.1 g of the trans isomers (yield 68%), which was the target product. This compound was in a liquid form at temperatures down to -60° C.

Workup

  1. customThe silacyclohexane rings of the target product thus obtained
  2. additiona mixture of trans isomers and cis isomers
  3. customAfter a conventional after treatment, they were separated by means of chromatography
  4. customto obtain 21.1 g of the trans isomers (yield 68%), which
  5. customwas in a liquid form at temperatures down to -60° C.

Sources & evidence

ORD record
ord-760829c21ce54e2585461d5d2f5cb8b3
Source dataset
uspto-grants-1996_03
Patent number
US05496501

Reaction notes

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