HCID 178418443, compound → HCID 178477601, compound

HRID 1377399Notes

Reaction equation

HRID 1377399 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CO[SiH:7]1[CH2:12][CH2:11][CH:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH:30]([F:32])[F:31])=[C:25]([F:33])[CH:24]=3)[CH2:15][CH2:14]2)[CH2:9][CH2:8]1>C1COCC1>[F:33][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][CH2:20][CH2:19][C@H:16]2[CH2:17][CH2:18][C@H:13]([C@H:10]3[CH2:9][CH2:8][Si@H:7]([CH2:1][CH3:2])[CH2:12][CH2:11]3)[CH2:14][CH2:15]2)[CH:28]=[CH:27][C:26]=1[O:29][CH:30]([F:31])[F:32]

Participants

4

Reactant 2

HCID 178418443HCID 178418443, compoundHCID 178503005HCID 178503005, compound

Product 1

HCID 178477601HCID 178477601, compoundYield 88.6%

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 42.9 g (10 mmols) of 1-methoxy-4-(trans-4-(4-(3-fluoro-4-difluoromethoxyphenyl)butyl)cyclohexyl)-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 such as removal of solvent and salts, followed by isolation through chromatography to obtain 37.8 g (yield: 88.6%) of the intended trans isomer product.

Workup

  1. additiona mixture of trans and cis isomers with respect to the silacyclohexane ring
  2. customThe product was subjected to ordinary aftertreatments such as removal of solvent and salts
  3. customto obtain 37.8 g (yield: 88.6%) of the intended trans isomer product

Sources & evidence

ORD record
ord-def5f2ac6fca41e18527ad93e2de86dc
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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