HCID 178418443, compound → HCID 178477599, compound

HRID 1377406Notes

Reaction equation

HRID 1377406 reaction equation
[CH2:1]([Mg]Br)[CH3:2].Cl[SiH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]([F:31])[F:30])=[C:24]([F:32])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:8][CH2:7]1>C1COCC1>[F:32][C:24]1[CH:23]=[C:22]([C@H:19]2[CH2:20][CH2:21][C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][C@H:9]3[CH2:8][CH2:7][Si@H:6]([CH2:1][CH3:2])[CH2:11][CH2:10]3)[CH2:17][CH2:18]2)[CH:27]=[CH:26][C:25]=1[O:28][CH:29]([F:30])[F:31]

Participants

4

Reactant 2

HCID 178418443HCID 178418443, compoundHCID 178505816HCID 178505816, compound

Product 1

HCID 178477599HCID 178477599, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

130 ml (0.13 moles) of a THF solution of 1M of ethylmagnesium bromide was dropped in a mixed solution of 43.3 g (10 mmols) of 1-chloro-4-(4-(trans-4-(3-fluoro-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 42.7 g (yield: 87%) of the intended trans isomer product.

Workup

  1. additiona mixture of trans and cis isomers with respect to the silacyclohexane ring
  2. customto obtain 42.7 g (yield: 87%) of the intended trans isomer product

Sources & evidence

ORD record
ord-848210852df447139d9fed0cd1629a10
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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