HCID 178418265, compound → HCID 178455406, compound

HRID 1377405Notes

Reaction equation

HRID 1377405 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH2:3][CH3:4].Cl[SiH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[CH2:10][CH2:9]1>C1COCC1>[F:32][CH:31]([F:33])[O:30][C:27]1[CH:28]=[CH:29][C:24]([C@H:21]2[CH2:22][CH2:23][C@H:18]([CH2:17][CH2:16][CH2:15][CH2:14][C@H:11]3[CH2:12][CH2:13][Si@H:8]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:9][CH2:10]3)[CH2:19][CH2:20]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 178418265HCID 178418265, compoundHCID 178506409HCID 178506409, compound

Product 1

HCID 178455406HCID 178455406, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50 ml (0.13 moles) of a THF solution of 2.5M of n-butylmagnesium chloride was dropped in a mixed solution of 41.5 g (0.1 mol) of 1-chloro-4-(4-(trans-4-(4-difluoromethoxyphenyl)cyclohexyl)butyl)-1-silacyclohexane and 30 ml of THF. The resultant product was found to be a mixture of trans and cis isomers with respect to the silacyclohexane ring. The product was subjected to ordinary aftertreatments, followed by isolation through chromatography to obtain 43.7 g (yield: 90%) of the intended trans isomer product.

Workup

  1. additiona mixture of trans and cis isomers with respect to the silacyclohexane ring
  2. customto obtain 43.7 g (yield: 90%) of the intended trans isomer product

Sources & evidence

ORD record
ord-320685f84b0447bfa671ad590be9f3c6
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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