Triethyl phosphite → HCID 178460916, compound

HRID 1080573Notes

Reaction equation

HRID 1080573 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][CH:18]([Mg]Br)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].I[CH:24]1[CH2:29][CH2:28][SiH:27]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]1.P(OCC)(OCC)OCC>[Cu]I.C1COCC1>[CH2:30]([SiH:27]1[CH2:28][CH2:29][CH:24]([C@H:18]2[CH2:19][CH2:20][C@H:15]([C:12]3[CH:13]=[CH:14][C:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=4)=[CH:10][CH:11]=3)[CH2:16][CH2:17]2)[CH2:25][CH2:26]1)[CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 31215Triethyl phosphiteHCID 123804129HCID 123804129, compoundHCID 178505500HCID 178505500, compound

Product 1

HCID 178460916HCID 178460916, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 25 ml THF solution of 1.0M 4-(4-(3,4-difluorophenyl)phenyl)cyclohexyl magnesium bromide (25 mmol) was dripped into a mixed solution of 5.36 g (20.0 mmol) of 4-iodo-1-n-propyl-1-silacyclohexane, 50 mg of copper (I) iodide, 100 mg of triethyl phosphite and 50 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 1.49 g (yield 36%) of the target product, i.e. the trans, trans isomers. The obtained target product exhibited the same physical properties as the product of Example 1.

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-c9b4909f2e1844fdabf2497940194c9b
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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