HCID 54305220, compound → HCID 178460932, compound

HRID 1077608Notes

Reaction equation

HRID 1077608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Mg]Cl)=[CH:4][CH:3]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][SiH:24]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:22]2)=[CH:15][CH:14]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>[CH2:27]([Si@H:24]1[CH2:23][CH2:22][C@H:21]([CH2:20][CH2:19][C:16]2[CH:15]=[CH:14][C:13]([C:9]#[C:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:18][CH:17]=2)[CH2:26][CH2:25]1)[CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 54305220HCID 54305220, compoundHCID 178505706HCID 178505706, compound

Product 1

HCID 178460932HCID 178460932, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

20.0 ml (30.0 mmol) of a tetrahydrofuran solution of 1.5M p-fluorophenylethynyl magnesium chloride was dripped into a mixture of 3.50 g (10.8 mmol) of 4-(2-(p-bromophenyl) ethyl)-1-n-propyl-1-silacyclohexane, 80 mg of tetrakis (triphenylphosphine) palladium (0) and 20 ml of tetrahydrofuran. The reaction mixture was stirred for 8 hours at room temperature. After a conventional after treatment, purification was conducted by means of silica-gel column chromatography to obtain 2.87 g (yield 73%) of the target product.

Workup

  1. customAfter a conventional after treatment, purification

Sources & evidence

ORD record
ord-40c4da581fa3432a98169b1931456e95
Source dataset
uspto-grants-1996_08
Patent number
US05543539

Reaction notes

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