HCID 178455855, compound → HCID 178460941, compound

HRID 1078161Notes

Reaction equation

HRID 1078161 reaction equation
Cl[SiH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3)[CH2:12][CH2:11]2)[CH2:4][CH2:3]1.[CH2:24]([Mg]Cl)[CH2:25][CH3:26]>O1CCCC1>[F:23][C:18]1[CH:17]=[C:16]([C@H:13]2[CH2:14][CH2:15][C@H:10]([CH2:9][CH2:8][C@H:5]3[CH2:6][CH2:7][Si@H:2]([CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4]3)[CH2:11][CH2:12]2)[CH:21]=[CH:20][C:19]=1[F:22]

Participants

4

Reactant 2

HCID 178455855HCID 178455855, compoundHCID 178505738HCID 178505738, compound

Product 1

HCID 178460941HCID 178460941, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixed solution of 3.7 g (10 mmol) of 1-chloro-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)-1-silacyclohexane and 30 ml of tetrahydrofuran (hereafter abbreviated as "THF") was prepared, and a 5 ml THF solution of 2.5M n-propylmagnesium chloride (12.5 mmol) was dripped into this solution. The silacyclohexane rings of the target product thus obtained were a mixture of trans isomers and cis isomers. Following a conventional after treatment, they were separated by means of chromatography to obtain 2.9 g of the trans isomers of the target product (yield 80%). The results of its analysis are shown below.

Workup

  1. customwas prepared
  2. customThe silacyclohexane rings of the target product thus obtained
  3. additiona mixture of trans isomers and cis isomers
  4. customwere separated by means of chromatography

Sources & evidence

ORD record
ord-a7e26ba3a2db46bab0404addc06c1557
Source dataset
uspto-grants-1996_08
Patent number
US05547606

Reaction notes

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