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

HRID 2167025

Reaktionsgleichung

Reaktionsgleichung von HRID 2167025
[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-585200e88f9d4e65844a353c1dd6a01d
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09044469B2

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