Boron trifluoride etherate → 2,2-Dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

HRID 626476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626476
[CH2:1]([Si](C)(C)C)[CH:2]=[CH2:3].[CH3:8][C:9]1([CH3:23])[CH2:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(O)[CH2:12][CH2:11][O:10]1.B(F)(F)F.O(CC)CC>C(Cl)Cl>[CH3:8][C:9]1([CH3:23])[CH2:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)([CH2:3][CH:2]=[CH2:1])[CH2:12][CH2:11][O:10]1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 641378172,2-Dimethyl-4-(4-methylphenyl)oxan-4-ol

Produkt 1

HCID 683142852,2-Dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Allyltrimethylsilane (4.34 ml, 27.2 mmol) was added to a solution of 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol (3.0 g, 13.6 mmol) in dry CH2Cl2 (100 ml) at 0° C., followed by BF3—OEt2 (3.42 ml, 27.2 mmol). The resulting mix was stirred at 0° C. for 1 h. The reaction was quenched with H2O (10 ml) and diluted with CH2Cl2 (10 ml), and washed with sat. NaHCO3 (20 ml), brine (20 ml), dried and concentrated. Purified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes) to give 2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane as a colorless oil, which was used crude (2.49 g, 75%).

Aufarbeitung

  1. additionThe resulting mix
  2. customThe reaction was quenched with H2O (10 ml)
  3. additiondiluted with CH2Cl2 (10 ml)
  4. washwashed with sat. NaHCO3 (20 ml), brine (20 ml)
  5. customdried
  6. concentrationconcentrated
  7. customPurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ab5a9e6708af427c81510088ef0cb82f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309234B2

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