Triethyl phosphite → HCID 131719726, compound

HRID 1901418Notes

Reaction equation

HRID 1901418 reaction equation
[CH2:1]([SiH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].BrCC[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH3:38])=[C:31]([F:39])[C:30]=2[F:40])=[CH:25][CH:24]=1.[CH2:41](OP(OCC)OCC)[CH3:42]>[Cu]I.C1COCC1>[CH2:1]([SiH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:41][CH2:42][C:25]3[CH:24]=[CH:23][CH:28]=[CH:27][C:26]=3[C:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH3:38])=[C:31]([F:39])[C:30]=3[F:40])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 31215Triethyl phosphiteHCID 5462224MagnesiumHCID 23367431HCID 23367431, compoundHCID 54274436HCID 54274436, compound

Product 1

HCID 131719726HCID 131719726, compound

Reagents, catalysts & solvents 2

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

Procedure

6.5 g (20 mmol) of 4-(4-n-pentyl-4-silacyclohexyl)-1-bromobenzene was dripped into a mixture of 0.5 g of magnesium (21 mmol) and 50 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 50 ml THF solution of 7.1 g (20 mmol) of 4-(2-bromoethyl)-2',3'-difluoro-4'-n-propoxybiphenyl and catalytic amounts of copper (I) iodide and triethylphosphite to obtain the crude product, which was a mixture of trans isomers and cis isomers with respect to the silacyclohexane ring. After a conventional after treatment, they were separated by means of chromatography to obtain 8. 3 g (yield 80%) of the target product, i.e. the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-956f25911dab43c783c1287fe9b4774a
Source dataset
uspto-grants-1996_11
Patent number
US05578244

Reaction notes

Loading…