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Tris(1,1-dimethylethyl)phosphine → 2-(2,4,6-Trimethylphenyl)-1H-indene

HRID 494681
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 494681
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[Mg]Br.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.Br[C:26]1[CH2:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2>C1COCC1.[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:26]1[CH2:34][C:33]2[C:28]([CH:27]=1)=[CH:29][CH:30]=[CH:31][CH:32]=2
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Komponenten

7

Edukt 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 5755861H-Indene, 2-bromo-HCID 178425415HCID 178425415, Verbindung

Produkt 1

HCID 598325532-(2,4,6-Trimethylphenyl)-1H-indene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 50.0 ml (20.0 mmol) of 0.4 M mesitylmagnesium bromide in THF, 230 mg (0.40 mmol) of Pd(dba)2, 162 mg (0.80 mmol) of PtBu3, and 3.90 g (20.0 mmol) of 2-bromo-1H-indene was stirred for 48 h at ambient temperature. Then, to the resulting mixture 200 ml of brine was added. The organic layer was separated, and the aqueous layer was extracted with 3×100 ml of ether. The combined organic fractions were dried over K2CO3 and then evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, 1 300 mm, eluent: hexanes-dichloromethane, 20:1, vol.). Yield 3.19 g (68%) of white solid.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 3×100 ml of ether
  3. dry with materialThe combined organic fractions were dried over K2CO3
  4. customevaporated to dryness
  5. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, 1 300 mm, eluent: hexanes-dichloromethane, 20:1, vol.)

Quellen und Nachweise

ORD-Eintrag
ord-5afa249002344910a885f29a22b974dd
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538168B2

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