Tetrahydrofuran → HCID 178439337, compound

HRID 1080572Notes

Reaction equation

HRID 1080572 reaction equation
C([Mg][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)CC.[Br-].CO[SiH:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.[CH2:33]1[CH2:37]OC[CH2:34]1>>[CH2:34]([CH:5]1[CH2:6][CH2:7][CH:8]([Si@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:9][CH2:10]1)[CH2:33][CH3:37]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 123941508HCID 123941508, compoundHCID 178455854HCID 178455854, compound

Product 1

HCID 178439337HCID 178439337, compoundYield 65%

Procedure

A 12 ml THF solution of 2.0M n-propylcyclohexyl magnesium bromide (24 mmol) was dripped into a mixed solution of 3.00 g (10.0 mmol) of 4-(4-methoxy-4-silacyclohexyl)-4'-fluorobiphenyl and 30 ml of THF. The silacyclohexane rings of the 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 2.57 g (yield 65%) of the target product, i.e. trans, trans isomers.

Workup

  1. customThe silacyclohexane rings of the 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

Sources & evidence

ORD record
ord-bbd5e3e5f182440fbf25148683c592e8
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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