Pyridine → (4-prop-2-ynylcyclohexyl)methyl Acetate

HRID 254141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254141
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C=O)C>[C:18]([O:11][CH2:10][CH:7]1[CH2:8][CH2:9][CH:4]([CH2:1][C:2]#[CH:3])[CH2:5][CH2:6]1)(=[O:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10796940(4-Prop-2-ynylcyclohexyl)methanol

Produkt 1

HCID 10726483(4-prop-2-ynylcyclohexyl)methyl AcetateAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 960 mg (6.31 mmol) of 86 in 6 mL DMF was added 0.62 mL (7.57 mmol) pyridine and 0.78 mL (8.27 mmol) acetic anhydride. The reaction was allowed to stir overnight at room temperature. After 16 hours, starting material still remained. The reaction mixture was heated at 75° C. for 3 hours. The solvent was removed under reduced pressure to yield a yellow oil which was purified by flash chromatography, on silica gel, eluting with 1:3 ether/petroleum ether to yield 1.12 g (91%) of 87 as an oil. 1H NMR (CDCl3) δ 3.87 (d, J=6.2 Hz, 2H), 2.06 (d, J=4.3 Hz, 2H), 2.03 (s, 3H), 1.98-1.93 (m, 1H), 1.92-1.83 (m, 2H), 1.83-1.74 (m, 2H), 1.63-1.36 (m, 2H), 1.12-0.90 (m, 4H); 13C NMR (CDCl3) δ 171.7, 83.7, 69.9, 69.6, 37.4, 37.3, 32.1, 29.7, 26.5, 21.4; APCI m/z (rel intensity) 195 (M+, 30), 153 (M+, 70), 135 (M+, 100).

Aufarbeitung

  1. waitAfter 16 hours
  2. temperatureThe reaction mixture was heated at 75° C. for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. customto yield a yellow oil which
  5. customwas purified by flash chromatography, on silica gel
  6. washeluting with 1:3 ether/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-6d77850011b54f469f4ad731d290e3fd
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875595B2

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