Bicarbonate Ion → 1-But-3-enyl-4-cyclohexyl-benzene

HRID 237883

Reaktionsgleichung

Reaktionsgleichung von HRID 237883
[CH:1]1([C:7]2[CH:28]=[CH:27][C:10]([CH2:11]OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:29]([Si](C)(C)C)[CH:30]=[CH2:31].C[Si](OS(C(F)(F)F)(=O)=O)(C)C.C(=O)(O)[O-]>COC(OC)C>[CH2:11]([C:10]1[CH:9]=[CH:8][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:28][CH:27]=1)[CH2:31][CH:30]=[CH2:29]

Komponenten

6

Edukt 4

HCID 769Bicarbonate IonHCID 65367Trimethylsilyl triflateHCID 69808AllyltrimethylsilaneHCID 68529340Diphenyl-phosphinic acid 4-cyclohexyl-benzyl ester

Produkt 1

HCID 866402421-But-3-enyl-4-cyclohexyl-benzeneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 107951,1-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred mixture of diphenyl-phosphinic acid 4-cyclohexyl-benzyl ester (1 g, 2.56 mmol) and 1.22 ml (7.69 mmol) of allyltrimethylsilane in 12 ml of dry dimethoxy-ethane at 0° C. was added 0.46 ml of trimethylsilyltriflate. The mixture was stirred at 0° C. for 1 h, poured into saturated bicarbonate, extracted with ethyl acetate, washed with water, dried (sodium sulfate) filtered and concentrated. The material was purified by chromatography on silica gel, eluting with ethyl acetate/heptane to provide 0.45 g of the title compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified by chromatography on silica gel
  7. washeluting with ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag
ord-4eae31e673ae496d881f5e6693c56fa0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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