Thionyl Chloride → 5-(Chloromethyl)-2,3-dihydro-1h-indene

HRID 869854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869854
S(Cl)([Cl:3])=O.[CH2:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14]O)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1>C(Cl)(Cl)Cl>[Cl:3][CH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[CH2:5][CH2:6][CH2:7]2

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 330183(2,3-dihydro-1H-inden-5-yl)methanol

Produkt 1

HCID 2331495-(Chloromethyl)-2,3-dihydro-1h-indeneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Thionyl chloride (120 ml, 1.65 mol) was added drop-wise to a rapidly stirred mixture of (2,3-dihydro-1H-inden-5-yl)methanol (81.4 g, 0.55 mol) in chloroform (500 ml) at 0° C. After the addition was complete, the resulting mixture was allowed to warm to room temperature and the stirring was continued for an additional 12 h. The chloroform was evaporated under reduced pressure to give a residue, that was purified by column chromatography (petroleum ether:ethyl acetate=15:1) to afford 5-(chloromethyl)-2,3-dihydro-1H-indene (90.5 g, 99%). 1H NMR (300 MHz, CDCl3) δ 2.06-2.19 (m, 4H), 2.93 (t, J=7.5, 4H), 4.54 (s, 2H), 7.15-7.31 (m, 3H).

Aufarbeitung

  1. additionAfter the addition
  2. customThe chloroform was evaporated under reduced pressure
  3. customto give a residue, that
  4. customwas purified by column chromatography (petroleum ether:ethyl acetate=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-4a3756c987734f16ae59478bb5fb46b7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969386B2

Notizen zur Reaktion

Wird geladen…